


Please Keep My Secret

by The_Littlest_Raindrop



Category: Kuroshitsuji | Black Butler
Genre: Blow Jobs, Caning, F/M, Fingering, Mildly Dubious Consent, Public School Arc, Reader Is A Girl Pretending To Be A Boy, Reader Likes To Be Punished, Sebastian Finds Out, Sexually Inexperienced Reader, Sexy Blackmail Ensues, Student Reader, Student x Teacher relationship, Teacher Sebastian Michaelis, reader is eighteen
Language: English
Status: In-Progress
Published: 2017-12-09
Updated: 2019-01-02
Packaged: 2019-02-12 08:22:43
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 8
Words: 23,802
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12955212
Author URL: https://archiveofourown.org/users/The_Littlest_Raindrop/pseuds/The_Littlest_Raindrop
Summary: As a child, your father had enrolled you in the prestigious Weston Collage, the best all-boys school in London. You're eighteen now, and so far things have been going great. There are only two problems;1) You're a girl2) Your new Housemaster knows itWhat lengths are you prepared to got to in order to convince Housemaster Michaelis  to keep your secret?





	1. The New Housemaster

**Author's Note:**

> Hey dudes,
> 
> I present to you a brand new story, because it came into my head and I couldn't control myself! This one is based around one of the manga arcs, but it won't follow it all that much, so this story can be read without prior manga knowledge :)
> 
> For anyone who's never read anything of mine before, I shall tell you now that this is Un-beta'd, so there may be a few mistakes littered here and there, though I do hope it won't be anything too egregious :/
> 
> Finally, for those of you wanting smut, it shall be in the next chapter, which I shall have up next week if all goes to plan.
> 
> Right, I'll shut up now. I hope you enjoy :)

It’s just your average day at Weston Collage. Students are scurrying about, Prefects are shouting at the scurrying students, Teachers are praising the prefects for doing their jobs properly…

Then there’s you. You, who has yet to get out of bed. 

It isn’t your fault that you overslept, although it doesn’t really matter. You don’t have to attend classes any more, so long as you study to make up for any absences. Ah, the perks of being in your final year. The other boys should have taken the time to wake you, though. Honestly, does no one respect their peers nowadays? Still, them not being in the dorm right now does make things a little easier…

You look around before you leave your bed, ensuring that none of the other students are around to watch you getting dressed. Privacy isn’t something that concerns most of the students here; an added bonus to being part of an all-boys school. No one here has to worry about any girls watching them get dressed, or being exposed to any women doing the same. 

At least, that’s what they all think. In reality, there is one student who isn’t quite as… masculine as the others. That’s to say, they’re not masculine at all; they’re a woman. How do you know this?

You are that woman.

You see, as your father’s only child, you are to inherit everything he owns, including his business assets. You can’t run a business without a decent education, yet al of the all-girls schools in the area were unsuitable. The focused on teaching manners and etiquette, not business skills and actual knowledge. So, your father had come up with a clever scheme. He had instructed you to pose as a boy, and enrolled you here as soon as you’d turned eleven. At first, you’d thought this stupid plan of his would backfire. Surely, the staff weren’t stupid enough to fall for such a thing? 

Apparently they were, and still are. You’ve been here for seven years now, and no one has figured it out. 

Things are obviously more difficult now than they had been in the beginning. Ever since you hit puberty, your body has begun to change dramatically. The most troublesome thing was your menstruation, which visits you once a month like some kind of curse. You fear discovery every time, but so far you’ve managed to conceal them. Not that you haven’t had a few close calls. About a year ago, one of your peers had caught you trying to clean blood off of your underwear. Without thinking, you’d blushed scarlett, and told him you’d had an ‘accident’ while ‘relieving’ yourself. He’d understood your excuse immediately, and even helped you clean away the blood. ‘The same thing happened to me once. Gotta be careful not to tug it so hard, you know? Try spitting on your hand, or using some cream or something.’ You’d nodded, and pretended to understand him. That was enough for him. 

Your cycle wasn’t the only issue. You had two other issues, both situated on your chest. Yep, your breasts had began to form at age thirteen, and now they’re so big you can’t even fit them in your hands any more. Not that you’ve ever tried that… okay, maybe you’ve tried it a few times, but only out of curiosity. They’re so big that you’d had to learn how to bind them to your chest to stop other students notice them. The binding feels uncomfortable, especially when your breasts are sore thanks to hormones, but it’s something that has to be done. You’d hate to be found out because someone had decided to stare at your chest for some reason.

With the coast apparently clear, you finally leave bed, and begin to dress yourself with as much haste as possible. 

Your uniform actually feels rather comfortable, even if your don’t like it all that much. It’s a stuffy suit and tie, standard uniform for an institution such as this. The only thing that distinguishes it from any other uniform is the tie, which is one of four colours, depending on the house of the wearer. As a member of the Sapphire Owl house, your tie is blue. The Owls are known for being studious, so you wear your tie with pride, always trying to live up to that image. You’re doing well so far, as your grades put you in the top five percent of all students. Your father had been delighted when you’d told him that, proudly stating that he thinks you’re the best child a man could ask for. It hadn’t escaped your notice that he’d said ‘child’, rather than ‘daughter’, but you had no desire to nitpick. Instead you’d basked in the affection he’d shown, and vowed to do even better this year.

Not a moment after you finish dressing, one of the younger boys bursts into your dorm room. He starts shouting as soon as he sees you. ‘There you are! The older boys asked me to look for you. They need you to come to the main dorm room straight away. Apparently, we’ve got a new Housemaster, and he wants to meet everyone. He’s really strict, so you should probably hurry. Sorry for disturbing you!’ You’re about to put on your gruffest voice and answer him, but he’s gone before you open your mouth. Honestly, youngsters these days…

You exit the same way the boy entered, thoroughly looking forward to meeting this new ‘Housemaster’ of yours. You’re glad they’re finally seen fit to replace the last one, as he really wasn’t up to much. Old, lazy, and perpetually hungry. Hardly fit to work in a place like this. This place has very high standards to maintain, so you hope that this new Housemaster is up to it. 

You begin to wonder what this new Housemaster will look like. He’ll be middle-aged at least, with a temperament as receding as his hairline. He’ll almost certainly be a little bit on the portly side, and his face will be ruddy at all times due to him constantly berating his charges. You wonder if he’ll subscribe to physical punishment, or if a stern telling off will be his weapon of choice. You’re glad that the faculty here consists of really unattractive men, otherwise the thought of a little punishment would probably be enough to keep you awake at night pleasuring yourself, something that would not end well. Thankfully, in a school full of teens and the aforementioned unattractive men, your urges have been easy to control. Every time you feel frisky, you just think of one of the teachers in the nude. That’s about a thousand times more effective than an ice bath…

You’re so lost in your thoughts that you forget to watch where you’re going, and end up walking right into someone. Said someone happened to be carrying a stack of books, all of which fall onto the floor. Your face flushes red with embarrassment, and you instantly fall to the floor, gathering up the stranger’s books without even looking at him.

Surprisingly, the stranger makes no move to assist you. Instead he just stands there, watching you. Normally, you’d glare at them, or verbally insist that they help you. However, as you’re very much the one in the wrong here, you bite your tongue. You’re certain they’ll at least thank you for your efforts.

You somehow managed to gather up all of the books. You stand with difficulty, unable to use your arms for balance. As you hand the stranger his books, you finally get a good look at him.

Looking at him turns out to be a big mistake.

Black hair, crimson eyes, kissable lips… this stranger is the most attractive man you’ve ever seen in your life. He has a pair of spectacles perched on the tip of his nose, which somehow only adds to his appeal. When your eyes meet, his isn’t looking through them though. He’s looking straight at you, almost as if he’s staring into your soul. You open your mouth to speak, but find that all of your words are lost. His good looks have rendered you speechless, as cliché as that sounds.

Your appearance hasn’t had the same effect on him, as he speaks to you with ease. ‘You really must learn to watch where you’re going. You’re lucky I wasn’t carrying anything fragile, or else this could have been a lot more serious. Now, will you kindly show me to the main dorm room? I have an urgent appointment to keep.’ Unbelievable. Not even so much as a ‘thank you’? What a rude man. You’d be tempted to tell him to shove off, if you could talk. Alas, speech is still just beyond your remit, so you nod, and continue on you way to the dorm.

The man follows you in silence, though you’re sure you can feel his eyes on you the whole way. Who is he anyway? Is he a parent? He can’t be a new student, he looks far too old. Well, actually, his age is difficult to place, but he looks older than collage age. Unless they’ve decided to let in a mature student? Nah, not likely. This place is far too traditional to allow something like that. So who is the then? 

You guess you’ll find out soon; you’ve arrived at the main dorm room.

The room itself is rather large, and inexplicably filled with armchairs and tables. Well, perhaps not so inexplicable, given how much everyone here likes to study. Speaking of everyone, your fellow classmates are currently stood directly opposite you, apparently awaiting your arrival. One of them steps forward, and you can’t help but shudder a little. It’s Lawrence Bluewer, your house Prefect!

He scowls at you. ‘Where on Earth have you been? Our new Housemaster is due any minute! It’s disgraceful, really. I only hope he doesn’t find out about this.’ You hear a deep chuckle, coming from the man stood behind you. He moves to stand a few meters next to you, and turn to face him, the other students following suit. 

He clears his throat. ‘I’m afraid it’s a little too late for that. I am Housemaster Michaelis. It’s nice to meet you all.’ He looks you dead in the eyes again, and your blood runs cold.

Oh, shit.


	2. Punish

**Notes for the Chapter:**

> Hello,
> 
> I hate leaving people waiting, so have some smut :3 I hope you all like it. I've tried to make it as consensual as possible, given the circumstances, but the consent may seem a touch dubious. If so, I do apologise.
> 
> Here we go :D

You messed up. You messed up big time. This is not how you imagined you’d meet the new Housemaster. He’s not how you imagined him to be. Today is full of surprises, although they don’t seem like the nice kind.

Housemaster Michaelis continues to look you in the eyes as he speaks. ‘My, my. Two misdemeanours in less than an hour. What do you have to say for yourself, boy?’ Boy? Who does he think he is? You’re eighteen, not eight! Why is addressing you like he would a naughty child?!

You hold your tongue again. As he’s already mentioned, you’ve messed up twice already today. A third strike will almost certainly land you in a whole heap of trouble. 

You put on your most sombre expression, and make your voice sound as low as possible. ‘I’m sorry, sir. It won’t happen again.’ You swear you see him smirk a bit, but you can’t be certain. It could just be your mind playing tricks on you.

‘I hope not. Three strikes warrants a punishment, and I would so hate to punish someone on my first day. Now, there is a reason I’ve asked you all here...’ His eyes roam over the other students, and you let out a breath you didn’t even realise you were holding. His stare is captivating. You’ll have to make sure to avoid his eyes at all costs, lest you forget yourself. It’s going to be that much harder to contain your femininity with such an attractive man in the dorm. You’ll have to make sure that your every step is acted out with caution, and with prior thought…

Housemaster Michaelis’ voice breaks your chain of thought. ‘As you are all in your final year at this institution, I feel that it is my duty to prepare you for life outside of these ancient halls. However, in order for me to help you, I’ll need to learn a little more about each of you. Therefore, I invite each of you to attend a small one-on-one conversation about your futures. I shall call your names out one at a time, and you shall follow me into my office. When our business is concluded, you are free to spend the rest of the day as you see fit, though I must insist that you do some form of studying at some point. Of course, you aren’t required to talk to me. You’re all more than welcome to leave. Except you, of course,’ He looks at you again, and you look him into the eyes. Damn it, whatever happened to your plan?

He holds your stare for a few tense moments, before turning his attention back to your peers. ‘Right, let us commence our sessions. I’ll begin with Bluewer, if that’s okay with you?’ Bluewer nods, and follows Housemaster Michaelis into his office, which is situated just off of the main dorm area. 

The remaining boys look around at each other, each of them wondering what to do. Most of the boys wander off, citing the need to study or some such thing. The remaining few all sit down, chattering quietly amongst themselves. You sit some distance from them, deliberately choosing to sit close to the office. With any luck, the Housemaster will call you in next, then you’ll be free to go about your day as originally planned; studying, and trying not to think about attractive men.

That last one is going to be difficult now, but you’re sure you’ll manage. After all, you’ve coped so far. One man can’t ruin your resolve in a single day, can he?

You think back to Housemaster Michaelis’ eyes, and realise that he might just be able to.

\------------------------------------------

The Housemaster calls each of the boys into the office one by one, just as he’d said he would. It’s taken him a few hours, but now he’s almost done. He only has one student left to interview.

You.

Yes, it seems that the Housemaster is determined to punish you after all, as he’s deliberately left your interview until last (at least, you suspect it’s deliberate. You don’t actually have any proof.). You’ve wasted most of your day in the main dorm, listening to idle chatter and twiddling your thumbs. It’s been very trying, yet you’ve remained still, not wishing to earn a third strike from the Housemaster. You’ve yet to get on the wrong side of any faculty member, and you’d hate to start that now. You don’t want to draw too much attention to yourself, after all…

Finally, the office door opens, and your classmate leaves it. He approaches you, a huge grin plastered on his face. ‘The Housemaster will see you now. Don’t be nervous, he’s such a nice man. He’s offered to help me with my Latin studies whenever I need. I’m sure he isn’t angry with you any more.’ That doesn’t seem likely, but you smile back anyway, leaving your seat and heading to the office.

You notice that the previous student has left the door ajar, so you walk right in, expecting the Housemaster to invite you to take a seat. Instead, he tuts loudly, eyeing you from behind his desk. ‘We do not enter someone else's office without knocking. Go back outside and request entry, or I’ll bend you over this desk, and give you the beating that you so clearly desire.’ His tone is imperious and harsh. It excites you more than you’ll ever care to admit.

You do as instructed, leaving his office and closing the door behind yourself. You knock three times, and patiently wait for him to grant you entry. ‘Enter.’ He calls out from the other side of the door. This exercise seems so futile, but you still don’t wish to provoke him. Or do you…?

‘No, you don’t!’ Your inner voice tells you. ‘I don’t care how sexy he is, or how frustrated you are. If he finds out you’re a woman, you’re in a whole heap of shit. So keep your head down and your legs crossed, and pray to God he doesn’t stare at you for too long!’ Your inner voice tends to give you pretty sound advice, so you decide to follow it, silently vowing to be a perfectly well-behaved pupil. 

You walk in again, automatically closing the door behind yourself. ‘There, that wasn’t too hard, was it? I’ll overlook that particular indiscretion, but I’ll remind you that you’re currently skating on very thin ice. Sit.’ He gestures to the seat just on front of his desk, and you follow his instructions with as must haste as you can.

He looks down at a piece of paper in front of him, one that has your name on it. Well, not your real name, but the name your father had chosen to enrol you with. John Smithy. How utterly original. All the staff in this school really must be stupid…

Housemaster Michaelis picks up a quill, dips it in ink, then looks at you again. You lick you lips subconsciously, your body apparently determined to ignore your inner voice.

The Housemaster begins talking. ‘So, Master Smithy, why don’t you start by telling me why you’re here at Weston Collage. What is it that you hope to gain from your time here?’ That’s a fairly standard question, one that doesn’t ring any alarm bells.

You answer him honestly, ensuring that your voice is masculine in tone. ‘I intend to take over my father’s company when he retires.’ Housemaster Michaelis nods, and begins to write something down on the paper before him. He seems to be writing far more than you’ve just said, which piques your curiosity. You’d try to read his writing, but refrain from doing so for fear of punishment. 

When he finishes writing, he starts speaking to you again. ‘What a remarkably clichéd answer. I was hoping for something a little more original, boy. Ah, such a pity. I doubt that there’s much I can do for someone as plain and unambitious as you.’ He’s baiting you. He has to be. He’s still fully determined to punish you. You won’t allow yourself to fall for it.

You keep your voice deep and expression neutral as you reply. ‘That’s okay, sir. There are so many boys here, it seems a shame to waste your effort on me.’ There, you bet he wasn’t expecting that!

He smirks at you. ‘There are indeed many boys here. However, as there is only one girl here, perhaps I should pay her special attention, after all.’ Your blood runs cold; has he figured out your secret already? Impossible, he couldn’t have! The people who have known you for the last seven years don’t even know that! Maybe his eyes truly can see into your soul. 

You decide to feign ignorance. ‘But sir, this is an all-boys school. There aren’t any girls here, that’s against the rules.’ 

His smile is equal parts unnerving and arousing. It’s the kind of grin that promises to devour you whole, yet silences any protests with the promise of pleasure. ‘Lying now, are you? That’s three strikes, and you know what that means. Bend over the desk and pull down your trousers and underwear. A good caning should sort you out.’ This isn’t happening. This isn’t happening! Only, it really is happening. Well, unless you can stop it happening.

Housemaster Michaelis stands up, and produces a cane from under the desk. Has that been there this whole time? He really has been looking for a reason to punish you! 

He begins walking over to your side of the desk. You stand automatically, trying to think of something to say to him. Will a simple apology suffice? Probably not. Teachers are well-known for never rescinding the threat of a physical punishment. If you were a boy, you’d take the punishment without a seconds thought, eager to be done with it. As you have just been exposed as a girl masquerading as a boy however, your position is slightly more precarious. 

You blurt out the first thing that springs to mind. ‘Please, sir, I’m sorry for lying. My father made me dress like this, made me pretend. Please don’t tell anyone.’ You don’t know why you’re even saying that. It’s not like he’s threatened to do such a thing, nor is it likely that your words will have any effect on him. He’s a teacher, after all. He’s obviously going to report you the moment he’s through punishing you!

He seems to consider your words, absent-mindedly twirling the cane in his hands. He clearly thinks of something interesting, as he stops twirling and smirks at you. ‘I think I have an idea that’ll suit both of us. If you agree to take my punishment, I shall delay telling the Headmaster your secret for a while. I’ll even be willing to throw in a little extra reward for you, if you take my punishment well enough. What do you say?’ His offer sets your mind racing.

On the one hand, you don’t like the idea of being blackmailed like this. If this were any other situation, you’d come clean yourself, if only to deny your blackmailer the satisfaction. Then again, this isn’t any other situation, and you’re not in a position to do such a thing. If you’re exposed, you’ll lose everything you’ve worked for these last few years. Not to mention the possible criminal charges that could be brought against you and your father. The shame of such a thing would almost certainly ruin your family…

On the other hand, this whole situation isn’t quite as bad as it could be. After all, you’ve always secretly fantasised about being punished by a handsome teacher. This could the fulfilment of that fantasy, while also ensuring that your secret remains just that; a secret. 

With that thought in mind, you give Housemaster Michaelis your answer. ‘If I let you punish me, you truly promise not to tell the Headmaster about me?’ You bite your bottom lip, trying to look both innocent and seductive at the same time.

He peers deep into your eyes. ‘You have my word, and I never lie. Now, if would be so kind as to assume the position I mentioned earlier, we can get this over with quickly.' 

You do as instructed, pulling your entire bottom half down. You bend over the desk, and subconsciously spread your legs, trying to keep balance.

He gives you no warning before hitting you.

The first hit stings worse than you ever thought it would. You’re finally beginning to understand why it’s considered to be one of the most effect form of discipline in schools.

The second his also stings, but it brings with it a sensation you can’t describe.

By the fifth hit, you figure out what that sensation is; arousal. Being punished is turning you on, just as it did when you fantasised about it.

When the seventh hit lands, you thank him for it. He gasps, caught off-guard by your comment.

The next hit is harder than any of the others. You love it.

He stops after the tenth. You can’t contain the small whine that escapes your lips as he tells you what a good girl you’ve been, accepting your punishment so bravely.

His hands slips between your legs. You can hear how wet you are down there, his hand movements creating the most delightfully obscene noises you’ve ever heard in your life. He slips a finger inside of you, and you bite into your arm to stifle a moan.

Housemaster Michaelis grabs hold of your hair, and pulls it back, allowing the tail end of the moan to escape. He sneaks another finger into you as he starts speaking. ‘If I can’t hear you, how will I know if you’re enjoying your reward? Feeling your nice wet quim around my fingers is one thing, but hearing you is something else entirely. Tell me, has anyone ever taken you to bed?’ It’s really hard to focus on answering his question with him pleasuring you like this, but you give it your best try.

‘No, si-ahh.’ You let out another moan, and begin to feel your entire body heat up. Your breasts ache within the confines of their binding, practically begging to be released. You’re not entirely sure what’s happening to you, but you’re loving every second of it.

Your Housemaster inserts a third finger, and brings his free hand around to toy with the little bundle of nerves a few inches above your opening. You’ve never had the guts to do that to yourself before now, which is something you regret immensely; it feels wonderful. 

You barely hear his next words. ‘My, how wonderful. To think that you’re still pure, even after spending all this time around boys. It’s enough to make me want to corrupt that purity, but I shan’t. I want you to beg me to take your maidenhood from you, to fall onto your knees and plead with me until I finally agree to fulfilling your desire. You’ll look so wonderful with me buried deep inside on you, finally discovering what it means to be a woman. I wonder if you’ve ever taken the time to try and discover that for yourself. If so, then I’m sure you know what you’re body’s about to do. If not, then I suggest you prepare yourself, for you are about to feel a pleasure that is unlike anything else in this world. It is called a climax, and you’re going to love it.’ He starts to move both of his hands faster, which seems to trigger something deep inside you. Your whole body goes ridged, as the pleasure the Housemaster spoke of washes over you, reducing all of your thoughts to nothing.

A cry escapes your lips, one you hope no one else hears. It’s the most feminine sound you’ve ever made, and that makes you feel wonderful.

Eventually, the feeling of pleasure eases off, as does your Housemaster. He slowing removes his hands from you, licking them clean of your essence. You turn your head just in time to watch him do it, and the sight is almost enough to make you… what did he call it? ‘Climax’? Again. 

You begin to pull up your bottoms gingerly, keeping your eyes on his just to see if he’ll berate you for doing so. He doesn’t, so you figure it must be okay.

Your backside stings as you finally right yourself, the aftermath of the cane far more unpleasant than the actual caning. Still, you can’t say you’re too upset about it. It was totally worth it.

Housemaster Michaelis smiles at you, though the smile doesn’t quite reach his eyes. He speaks rather softly, which comes as a surprise, given the things he’s just been saying to you. ‘You took my punishment beautifully. Your secret is safe with me, for now at least. Why don’t you go and clean yourself up? I’d hate to see one of my students walking around looking so unkempt. I shall undoubtedly see you again before the week is out. Dismissed.’ He returns to his desk, leaving you to feel rather disoriented. You leave his office in a daze, desperately trying to figure out his last few sentences. 

What does he mean when he says he’ll keep your secret ‘for now’? Does that mean he plans to tell someone in the future? And was his farewell just a farewell, or was it a promise of sorts, too?

You head to the showers, deciding to take Housemaster Michaelis’ advice.

Today has certainly been interesting.

**Notes for the Chapter:**

> So, was that worth waiting for? I hope for, for there shall be more. Not for a few days though; I can't write this quickly all the time ;)
> 
> Hope to see you soon :)


	3. Private Tuition

**Notes for the Chapter:**

> Hey,
> 
> Sorry it's taken me so long to update. As I explain in the Broken Pieces A/N, I've been dealing with some mental stuff lately, so I haven't felt up to writing much. There should be more updates on everything soon though ^.^
> 
> Enjoy ;)

It’s only been three days since your encounter with your new Housemaster. Three long, nerve-wracking days. 

You haven’t seen much of the man since that day. He’s spent most of the time in his office, almost certainly focusing on settling in properly. The only times you’ve seen him outside of said office is during school assembly, and even then he seems like his mind is elsewhere. You can’t decide if his lack of presence in the dorms is a good thing or not. 

On the one hand, if he’s cooped up in his office, you don’t have to go out of your way to avoid him. What happened three days ago was… well, it was wrong. Sinful, shameful, divine… you don’t think you’ll ever be able to look Housemaster Michaelis in the eyes ever again, not without imagining his hand between your legs. Honestly, the way that he made you feel… you hate to admit it, but you’ve never felt more alive than you did in those few moments. The pleasure was almost unreal, and a part of you is desperate to feel it again.

On the other hand, if you can’t speak to him, how will you know if he’s told the Headmaster your secret or not? He’d told you he wouldn’t, but how long will his silence last? He’s a teacher, after all, and it’s his duty to inform the Headmaster if anyone has broken any cardinal rules, or anything else along those lines. As The Bard once said, ‘Truth will out’, and you’re terrified that yours will be out before you get the chance to finish your education.

These thoughts have been circling in your mind for the last three days, making concentrating on things difficult. More than once you’ve been caught staring dreamily out of the windows, and you’ve almost bumped into just about every other dorm member. Then there’s your dreams; your wild, erotic dreams, the kind that make you want to call out your Housemaster’s name in pure ecstasy. Those dreams are the most dangerous things, as it’s hard to interpret a wanton moan of someone’s name as anything other than a sexual thing. If one of the boys hears you… 

You know in your heart that you have to pay the Housemaster a visit, for the sake of your mental well-being. You need to know what he plans to do with you, and when he plans to do it. The uncertainty is the thing that’s bothering you the most, and you know that talking to him is the only way to rectify that.

\-------------------------------------------------------------------------------------------------------------------

It’s late afternoon, and most of the boys are outside, soaking up what is sure to be the last of the sun’s rays before winter sets in. You have no time for such frivolity; you have a Housemaster to talk to.

You make your way to his office, hoping that no one notices you. You’d hate to have to lie to someone about why you wish to meet with your Housemaster. What could you tell them? Your grades are excellent, so it’s not like you need extra tuition. Still, that’s a much better reason to give than ‘he knows I’m a woman, and I want to find out if he’s going to tell the Headmaster’. You’d be expelled on the spot.

Mercifully, the faculty also seem to be occupied today, as your journey to the office is competed without interference. 

You hesitate outside the door. Are you really about to do this? Are you really about to voluntarily put yourself in a situation where you’re alone in an office with an attractive member of the opposite sex? A member who, on your last visit to this office, made you feel incredible? How are you supposed to question him when all you’re going to be able to think about his how amazing his fingers felt when they slipped inside you. Would he be willing to do that again maybe? You doubt it. That was a one-off, you’re certain of it. He wouldn’t do something like that again. He might be a man, but he’s also a professional. You’re unlikely to do anything sexual with him a second time.

You push all of your thoughts away, take a deep breath, and give the door a firm knock.

His response is almost immediate. ‘Enter.’. Well, here goes everything.

Slowly, you open the door, your heart beating faster than ever before. How will he react to seeing you again? Will he be pleased? Surprised? Angered? Will this only make things worse?

You close the door behind you, and your eyes immediately fall on Housemaster Michaelis.

The man is sat there, several of his shirt buttons undone, casually going over paperwork. His hair dark hair is dishevelled, his glasses are precariously perched on the edge of his nose, and you can he the top of his pecks thanks to his lack of buttons. To put it bluntly, he looks sexy, and you’re suddenly finding concentration very difficult.

When he looks up from his paper to see who’s decided to pay him a visit, he smirks. ‘Well, this is a pleasant surprise. I was rather hoping you might pay me another visit soon. Still, I was thinking it would take longer than three days for you to break. Do you truly desire my touch that much?’ You should be angry at him for assuming that is the reason you came here, but you can’t bring yourself to feel anything other than arousal. Why are you here, again? 

You shake your head, trying to clear your mind. ‘That’s not why I’m here, Sir.’ 

His raises his eyebrows. ‘Oh? That’s a pity, I was so looking forward to playing with you again. I even had the perfect little scenario all worked out in my head. I think you would look wonderful stretched out along my desk...’ Must he say things like that? He’s driving you mad! You have to fight the urge to rub your legs together, lest he find out just how much he’s affecting you.

You a deep breath. ‘I need to know when you plan to tell the Headmaster about me.’ 

Housemaster Michaelis’ smirk widens. ‘I wasn’t planning on telling him at all. Not while I still have my own plans for you. I’d be happy to tell you what those plans are, if you’d be willing to do something for me.’ The look in his eyes screams sex, and you’re certain his request is going to be completely obscene.

You move closer to him, your hormones hijacking your body. You’re more than willing to hear what he wants, and you want to hear what he has planned for you. After all, that is the purpose of this visit. You want answers, and he’s willing to give them to you, in exchange for a favour.

You stop just in front of his desk, biting your lip in anticipation. ‘What do you want me to do, Sir?’ Using the honorific like that makes you feel so dirty, but you can’t help yourself. He hasn’t told you to stop using it either, so he must like it too.

He crooks his finger, indicating that he wants you to come closer. You walk around his desk, stopping directly in front of him. Your body is practically touching his, which does nothing to sooth either your nerves or your arousal. 

He looks up at you, a glint of something devious in his crimson eyes. ‘Tell me, do you know what fellatio is?’ You think you’ve heard the term before, but you’re not certain what it means. You shake your head. ‘My, you really are a total innocent, aren’t you? On your knees, girl. I’m about to teach you something interesting.’ You comply without question, excitement building within you. 

Your new position puts your face directly in front of his crotch, a clear bulge visible in his crotch area. Housemaster Michaelis undoes his trousers, before pulling them and his underwear down to his knees. This allows his erection to stand to attention, free from any restraints. It’s the first time you’ve ever seen a penis up-close, and you can’t help but find it slightly intimidating; that’s supposed to fit between your legs?

Your mouth falls open in shock, which pleases the Housemaster. ‘I take it you’ve never seen an erection before, have you? No matter, you’ll be well-acquainted with mine before too long. 

‘Now then, why don’t I explain what I expect of you? You’re already part-way there; I’ll need you to keep that dainty little mouth of yours open for me, understand?’ You nod, keeping your jaw slack. ‘Good girl. Now, come closer. I want your head between my legs.’ Again, you comply, as you realise where this is going.

Sure enough, as soon as you’re in position, Housemaster Michaelis weaves a hand through your hair, and grips onto it tightly. ‘So obedient. Keep this up, and I might just have to reward you. Now, clever girl that you are, I’m sure that you’ve already figured out what comes next. Are you still willing to comply?’ He has really poor timing. As if you could really back out now! Just thinking about having his erection in your mouth is ruining your underwear!

You look up at him from under your lashes. ‘Yes, Sir.’ You answer, hoping you’ve conveyed just how much you want this.

The Housemaster wastes no more time, guiding your open mouth to his waiting tip. ‘Tease it with your tongue, girl.’ This new nickname of his is making you feel even filthier. Your tongue effortlessly leaves your mouth, and begins to swirl itself around the head of his length, the skin of it soft underneath your flexible muscle. 

Housemaster Michaelis’ grip on your hair tightens. ‘That’s it, good girl, I think you’re going to be a natural at this. Normally, I’d expect you to tease me more, but I fear you’ve gotten me rather flustered. Now, stop what you’re doing, and open wide again. I want to see how much of me you can take.’ Your tongue immediately halts its ministrations, returning to your now-open mouth. The Housemaster’s grip on your hair remains firm as he guides your mouth over his erection, before pushing your head down.

He manages to get about half of it in before you gag. He chuckles. ‘Not bad at all for a beginner. Now, I’m going to keep moving your head up and down, and I want to see if you can take me any deeper. If you can’t, don’t worry; I intend to train you. For now, just do the best that you can, while I tell you what I have planned for you. Oh, and feel free to slip a hand into your own under-things; I want you to learn how your body works. Consider this practical tuition.’ With that, he tugs your head back, his erection slipping out of your mouth with an obscene squelching. He wastes no time forcing it back in, as he begins to fuck your face in earnest.

You decide to take his advice, and slide a hand into your underwear. You’ve never touched yourself like this before, so you’re a little lost. You try to remember what Housemaster Michaelis had done to make you feel so good, but it’s hard to focus with him using your mouth like this. You can feel your jaw ache already, and you haven’t been at it for very long. How long will it take for him to reach a climax? Will he help you with yours after you’re done with his?

Certain that he will, you let your hand wander absent-mindedly around your opening, no longer aiming for anywhere specific. Instead, you focus on pleasing your partner, hoping that your efforts will be rewarded. 

The Housemaster lets a series of low moans, your efforts clearly appreciated. ‘That’s it, good girl. Such a good little whore. You were born to do this this. I’m going to have so much fun with you. Ah, that reminds me, my plans for you are as follows;

‘In exchange for keeping your dirty little secret, I expect you to report to this office at least once a week. I intend to use your body to pleasure myself, just as I am now. Fear not though, for I shall make sure that you are not left wanting. I may call you ‘girl’ now, but I will make you a woman. I have already told you I’ll have you begging for me, and I will. 

‘However, if you decide to back out of our agreement, or if you let anybody else know what goes on in these ‘private sessions’ of ours, I shall have to tell the Headmaster about you. I doubt he’d be willing to show you as much lenience as I have. So, does that answer your question, or do we need to do this again for my message to sink in?’ He pulls you off of his erection so you can answer him.

You take in a few breaths, glad that you don’t have to breathe through your nose for a moment. ‘I understand, Sir. You just tell me when you want me, and I’ll come to you.’ He’s blackmailing you again, and you know it, but it could be so much worse. So far, you’ve gotten some kind of perverse pleasure from all of this, and you’re certain it will only get better. Besides, this is a great opportunity to learn about sex, something that they don’t teach you in the classroom. Not only that, but having a faculty member who wants your secret to remain undetected can only be a good thing, can’t it? The situation seems like a win-win, and it would be foolish to refuse him. After all, what would your father think if you were kicked out of school? 

Housemaster Michaelis sets you to work again straight away, quickening his pace considerably. He seems to grow even harder, something you didn’t think possible. Does this mean he’s close to finishing?

The Housemaster starts moaning again, his voice strained. ‘Good girl. Now, I think it’s time we finished today’s lesson. Have you been playing with yourself as I suggested?’ Your hand had stopped moving ages ago, your mind focused solely on him. ‘If you haven’t, them I’m setting you some homework. You must bring yourself to climax at least once before your next visit. As I told you a moment ago, you need to learn how your body works. Can you do that for me?’ So he’s not going to help you out, after all? Bastard! Still, he didn’t say he was going to, you just assumed that he would. Guess it’s true what they say about assumption…

He doesn’t pull you of to answer this time; he apparently has another use for your mouth. Before you have time to register what’s happening, Housemaster Michaelis lets out a low groan, and your mouth begins to be filled up by some kind of liquid. You swallow it reflexively, cringing at the taste. It’s bitter, and just a bit salty. Not the worse thing you’ve ever had in your mouth, but definitely not the best. 

When the liquid is gone, your head is pulled back again, your Housemaster’s erection growing limp in front of you. It doesn’t look quite as intimidating as it did before, especially now that you’ve had it in your mouth. 

The Housemaster uses his thumb to wipe saliva from your lips, as he tilts your head up to face him. ‘You swallowed without prompting? You are the perfect plaything. We’re going to have such fun together. Now, why don’t you go off and do your homework? It’ll be best to do it while the lesson is still fresh in your mind, wouldn’t you agree?’ That may be the best advice you’ve had all day. 

‘I’ll be sure to do that, Sir. I’ll tell you how I got on next week.’ You offer him a sweet smile, which he devours with his eyes. Before he can say anything else, you exit the room, leaving the man to sort himself out.

As soon as you get out of the office, you feel your heart beat even faster. Did you really just agree to start an affair with your Housemaster?!

The dampness between your legs confirms that that is exactly what you just did.

**Notes for the Chapter:**

> So, random question for you guys (because I've had an idea, and I'd like to hear your opinions on it); if I was to involve Headmaster!Undertaker in this, how would you guys feel about that? Obviously, this will still be a Sebastian-centric stroy, and it would be little more than a smutty cameo, but what do you think? Yay or nay? I might end up doing it anyway, but if you're all dead against it then I won't ^.^
> 
> Hope you enjoyed this chapter, and I hope to see you all again soon :3


	4. Anatomy Lesson

**Notes for the Chapter:**

> Hey guys,
> 
> So sorry it's been so long. I've been finding writing rather hard lately :/ still, I hope you enjoy chapter four ^.^
> 
> Oh, and quick shout out to a friend of mine, LonelyStargazer. She has a Sebastian and OC character story called Wicked Game, which can be found on both this site and Fanfiction.net. So, if that sounds like your thing, be sure to give it a read ^.^
> 
> Right, NOW it's time for chapter four :)

It's now been a full week since your visit to your housemaster's office. One week of pining, sexual longing, and subtle experimentation late at night in your dorm. You've been set some very interesting homework, and you'd hate your housemaster to think you're not a dedicated study.

However, you've found yourself facing quite the problem; try as you might, you just can't reach climax as instructed.

As soon as you'd left Michaelis' office last week, you'd gone to the showers, hoping to find release there. Yet try as you might, you just couldn't bring yourself to ecstasy as he had the first time you visited his office! Your own hands felt no where near as sensual as his, which had caused you a great deal of frustration. In the end, you were so fixated on your own shortcomings that all of your arousal had dried up, and you found that any friction on your genitals caused you to feel sore, rather than aroused.

After that failure, you've tried every night to bring yourself to climax, but with almost identical results; you get yourself wet, you realise you can't pleasure yourself as well as your housemaster, you lose your arousal. It's beginning to drive you mad, your body so desperate for release. You'd give anything to be able to get yourself off, but you just can't manage it! 

That's why, with a great sense of fear and reluctance, you find yourself stood outside his office door yet again, trying to find the courage to tell him you've failed, and to beg him not to reveal your secret as punishment.

You've been outside said office for a good ten minutes now, your hands shaking. You're glad your fellow students are all busy doing things elsewhere, otherwise you'd look very strange indeed. You're not even certain your housemaster is in his office. He could be with the headmaster for all you know, telling him your secret…

No. He wouldn't do that. Not yet, at least… 

You take in a deep breath, trying to steel your resolve. Maybe he'll show you mercy if you do what you did last time? Fellatio, was it? Maybe if you offer him that, he'll go easy on you?

Curling your shaking hand into a fist, you raise it aloft, and direct it towards the door.

Before your hand has the chance to touch the wood, you hear a voice from behind it. 'Enter.' You recoil in shock; has he known about your presence all this time?!

After trying to physically shake off your nerves, you do as instructed, entering his office before closing the door behind you.

Contrary to the way he looked last time you visited him, Housemaster Michaelis looks flawlessly tidy. His bow tie is properly affixed to his fully-buttoned shirt, and his spectacles are right back against his face, as opposed to perched on the end of his nose. He looks the very model of propriety; that makes what you've come to talk to him about seem even more depraved.

Housemaster Michaelis smirks at you as always, a familiar twinkle in his eyes. 'Well, well. It seems my favourite pupil has come to pay me a visit. Tell me, did you complete your homework as instructed? You seemed so throughly aroused the last time I saw you, so I doubt you had any issues.' Shit, you really are in for it, aren't you? All these years of education ruined because you couldn't make yourself climax…

Fate is a bitch.

Swallowing reflexively, you hesitate a moment before answering, your voice little more that a whisper. 'Actually, Sir, I- I couldn't do it. I tried so hard, really I did! Every day I tried to make myself reach orgasm, but I just couldn't do it! I- I tried touching myself all over, I tried thinking about you… yet every time without fail I found myself craving your experienced touch, rather than my inexperience one. The frustration always makes me lose any arousal I've built up. I am so, so sorry. I'll do anything to make up for it.' You hang your head in shame. You hope that Housemaster Michaelis knows just how sincere you are, and that you really are willing to do anything to make things right.

Housemaster Michaelis stands, his height greatly intimidating. He walks around his desk, stands in front of you, and uses a single finger to force your eyes up to meet his own. 

His voice is as silky smooth as always. 'Dear Girl, it's alright. I have no doubt you tried your very best. Failure is as much a part of learning as success, so you shouldn't feel ashamed. If anything, the thought of you having to come to me in order to find release is quite delightful.' He plants a chaste kiss on your lips, and you feel your heart skip a beat. You're really not in trouble? Thank goodness!

Your housemaster's smirk grows wider. 'Speaking of which, I bet you're desperate for release, aren't you? Well, thankfully I could use a distraction; paperwork is so very tedious. I'll put my papers to one side so you can sit that perfect behind of yours on my desk. It's time for your next lesson. I think you'll enjoy this one.' With that, he removes his finger from beneath your chin, walks back over to his desk, puts his papers to one side as stated, and sits back down, before crooking his finger indicatively. Taking the hint, you walk over to him, and sit on his desk.

Almost immediately, Housemaster Michaelis' hands grab your thighs. 'Now then, lesson three is a practical anatomy lesson, followed by cunnilingus. Do you know what that means?' You've never heard the term before, but you think you can guess.

Trying not to sound as apprehensive as you actually are, you give him your answer. 'Is it a bit like what we did last time, but reversed? So your mouth and my… my… downstairs?' Well, so much for trying to sound confident. You can already feel your face beginning to heat up, and you've not even started your 'lesson'.

Your response earns your thighs a squeeze. 'You are quite correct, girl. However, I would not have but it quite like that. I would have said that cunnilingus is the act of someone placing their head betwixt a woman's thighs and tasting her quim until she begs for mercy. Points for trying, though. 

'Now, how about we take off these trousers of yours, hm? I think it's time we commenced this lesson properly.' Without waiting for a response, Housemaster Michaelis moves strait to the fastenings of your trousers. 

You can't help but feel a little giddy. Finally, you get the chance for release! You need it so badly it hurts! Even if the man about to pleasure you is technically blackmailing you…

All thought temporarily ceases when you feel the cold air of the room against you now-exposed opening. 

You gasp as you feel Housemaster Michaelis run a finger along your slit. 'Still so sensitive. I bet all of your failed attempts at masturbation have you on edge. Now, I'm going to fetch a mirror from my drawer. I'm then going to aim it between these sweet thighs of yours, and teach you all about the female anatomy. Pay close attention, as I'll be testing you the next time I see you. Now then, spread yourself as wide as you can, and put your feet on the desk.' You're glad that he had the foresight to remove your socks and shoes when he took your trousers and underthings, or this would be terribly uncomfortable and slippery. As it is, your bare feet hold firm on the table, as you position yourself as instructed on the desk.

Housemaster Michaelis produces a mirror as stated, and positions it just in front of your opening. You blush as you catch sight of yourself down there for the first time in your life; is that really what your opening looks like?!

A laugh brings you out of your temporary fixation with the image in the mirror. 'Dear me, have you never seen yourself like this before? Such a pity. A quim as beautiful as yours shouldn't be hidden away. It's almost enough to make me tell the headmaster the truth, if only so he'll get the chance to behold it.' You begin to panic at his words, until he continues. 'Alas, I do not share my prey. I am the only one that gets to touch you, just as I shall be the one to take your innocence.' As if to illustrate his point, he pushes his finger inside you, causing you to hiss at the slight ache.

Your reaction earns you a soft kiss on your knee. 'Relax, girl. Your purity shan't be tainted by me today. As tempting as that may be…' You watch in the mirror as he pulls his finger out of you, the obscene act making you even more desperate for release. All you want now is to get this first part over and done with, so that you can learn if your Housemaster is as talented with his tongue as he is his fingers…

Housemaster Michaelis begins by bringing his finger to a small nub a few inches above your opening. 'Now, this delightful little thing is called the clitoris. It's home to over 8000 nerve endings, and is comprised of the clitoral hood and the clitoral glands. Now, what do you feel when I stroke it?' He strokes his finger across it, and you can't help but cry out in pleasure. 'Pleasurable, isn't it? Stimulation of the clitoris is vital during coitus. However, overstimulation is to be avoided at all costs. If you are too rough with it, or toy with it for too long without applying proper lubrication, it becomes sore, and thus causes discomfort that can ruin any kind of sexual enjoyment. I imagine this is one of the problems you've been having.' He strokes it again, and your legs twitch. You hope he knows how much is too much…

Your housemaster's finger moves down slightly. 'These two flaps of skin are your labia minora. They cover and protect your clitoris when you're not aroused, and shift to expose it when you are. You also have their counterpart, the labia majora, which are these thicker ridges here. They serve a similar purpose.' He trails his finger straight past your opening, and onto the piece of skin just below it.

Housemaster Michaelis smiles to himself. 'This is the perineum. It separates your vagina from this hole down here.' His traces his finger around your anus, and you gasp. 

His smile transforms into a smirk. 'I'm sure you don't need me to explain what an anus is. However, I will tell you that the anus can be utilised during intercourse, both as a tool to create arousal, and as a point of entry. However, a virgin like you should not be sullied like that. No, I must wait until I have made you a woman before I do that to you.' He brings his finger back up to your opening, ceasing movement just below it.

You feel your body tremble as you watch him circling your opening in the mirror, fascinated by the reflection before you. You've always assumed that your genitals must look horrible, judging by the church's insistence that you must keep them hidden at all times. Yet seeing them like this, being caressed by another… they look quite delightful.

You're quickly snapped out of your thoughts when you feel his finger push inside you once again. 'This is the vaginal opening. This is where the act of sex itself takes place. It was specifically designed to take a man, and take a man you shall. For now though, I think my finger shall suffice.

'So, did you enjoy your guided tour? I hope you were paying attention, as it is your homework for the week to memorise the names of each part. I shall be testing you, of course. Should you succeed, I shall give you a reward. Fail, and I shall have to punish you again. Understood, girl?' 

You nod your head in response. That does not go down well.

With a heavy sigh, Housemaster Michaelis forces two more fingers inside you, causing you to cry out in pain; it aches so much!

He begins tutting. 'When I ask you a question, girl, I expect an answer. Now, do you understand?' He twists his fingers, and this time when you cry out it isn't entirely from pain.

You give him the response you assume he's after. 'Yes, Sir. Sorry, Sir. I swear not to do it again, Sir.' 

Housemaster Michaelis' smirk returns, and he removes two of his fingers. 'See how easy things are when you behave? I'm beginning to think you need more discipline, rather than a reward. Still, I did promise to demonstrate cunnilingus for you. Now, put your back flat against the desk and close your eyes. You are not to open them until you rach climax. If you do so beforehand, I will drag you off this table and force you to perform fellatio again. Is that understood?'

Not wanting to risk angering him again, you answer verbally. 'Yes, Sir.' You say, a little breathless, before getting into position as instructed. He hasn't told you to move your legs, so you keep them as they are, spread open for him. 

As you close your eyes, anticipation washes over you. Will it really feel nice? Will you taste alright? Will he even let you finish as promised?

Suddenly, you feel something wet against your clit, and you begin to lose all semblance of thought.

Housemaster Michaelis swirls his tongue around your clitoris, teasing it with what seems to be practiced grace. Your whole body seems to be heating up in response, and you're certain your arousal must be drenching his finger, as he gently begins moving it in and out of you.

His tongue begins to explore the rest of the area between your legs, flitting to one place before returning to your clit. You can already feel yourself working up towards orgasm, the frustration of failing to climax so many times on your own all seeking to culminate in one final explosion of pleasure. You prey that your orgasm really does come soon; you're not sure how many more failed orgasms you can take.

You feel a vibration against your clit, and realise that your housemaster has started talking. 'That's it, good girl. I don't think it'll be long now. You really shouldn't have waited a whole week to come and see me. Had I known what difficulties you were suffering, I could have helped you sooner. Then again, I suppose the fear of disappointing me kept you away. Probably just as well, really. Had I thought you had not been putting in the right amount of effort, I would have given you another caning.' 

Just the thought of him doing that to you again is enough to trigger your release, as you cry out into his office, really hoping that no one is outside. You really must find a more secluded venue to approach him in…

As the pleasure washes through your body, you feel your housemaster sneak in another finger. To your surprise, it doesn't sting like it did a moment ago…

When you finally come down, you hear a soft chuckle. 'Well done, girl. That concludes our lesson for the day. Now, if you'd kindly redress, I do believe I have paperwork to finish. I shall see you again in a week to test your anatomical knowledge. Dismissed.' 

You sit up on the desk, open your eyes, and let yourself off of the table and onto your trembling legs. They feel like jelly as you silently redress yourself, your housemaster watching your every move. You happen to notice there's a sizeable bulge in his trousers now, but you don't mention it. After all, he has it work to do, and so do you.

Once you're all put together again, you leave the office without looking back, and head straight towards the library.

After all, you can't really be expected to remember anything he told you; right now, you're amazed you even remember your name.

You just hope nobody in the library notices your trembling.

**Notes for the Chapter:**

> So, what did you think? I hope it was worth the wait :)
> 
> Hope to see you next time ^.^


	5. Insertion

**Notes for the Chapter:**

> Hey,
> 
> Here is the next chapter for you all. I’ve thankfully been on something of a writing streak for a few days; let’s see if it lasts :P
> 
> Enjoy ;)

This last week seems to have lasted forever.

After your anatomy lesson, you’d decided that it’s fruitless to try and remember exactly what your housemaster told you (especially since you were very distracted at the time), so you’d popped to the library, desperate to find a textbook with supplementary material.

That was a waste of time.

The librarian had eyed you with great distain when you’d asked if there were any books on female anatomy you could borrow. He’d said that such a book had nothing to do with your education, and then tried to shoo you away! When you’d told him that it was for person use, he’d grinned at you, then taken you to one side for a little chat about how unimportant it is to please a woman! He’d said that as long as you managed to knock her up, then everything else is irrelevant. He’d offered to give you a book on how children are made, but you’d turned him down; everyone with a brain could tell that babies are made via sex! 

You’d left the library quickly, and desperately tried to remember what you’d been told by Housemaster Michaelis. To your dismay, most of his lesson seems to have left your mind!

And so, you’ve spent all week desperately running around to your fellow classmates, asking them if they know anything about female anatomy. The ones that hadn’t laughed in your face had blushed crimson and turned tail, too prude to justify your question with an answer.

So, now you’re heading to your housemaster’s office, having once again failed his lesson. How many times is he going to be reasonable with you before he loses patience and outs your secret? Maybe if you plead with him on your hands and knees, he’d give you one more chance to please him…

You shake off that thought as you prepare to knock on his door, reaching your hand out. The door swings open before your fist makes contact, revealing none other than the school’s headmaster!

Realising who’s stood in front of you, you immediately straighten up, and try to act politely. ‘Good morning, Sir. I was just planing to ask Housemaster Michaelis to help me with my Latin. I can come back later.’ You’ve never seen the Headmaster up-close like this before, as he tends to keep his distance. From what you’ve heard, the only other students who get to stand this close to him are the ones he invites to his midnight tea parties, and you’ve never had an invitation.

The Headmaster, who has his fringe over his eyes, gives you a warm smile. ‘By all means, go ahead. I can’t have one of my best students falling behind. Would you mind coming to see me in my office when you’re finished though? I have something I’d like to discus with you.’ That sounds ominous. Hopefully it has something to do with your grades, rather than his meeting with your Housemaster. Surely he wouldn’t have told the Headmaster already?

You give the Headmaster a quick bow. ‘Of course, Sir. I’ll come as soon as I’m done here.’ Cooperation in this case is key, as anything else would only make him suspicious. Still, you really wish you didn’t have to see him…

The Headmaster offers you a tip of his hat before heading off in the direction of his office, apparently content to take you at your word. With him now gone, you’re free to enter the Housemaster’s office, and face the consequences of your bad memory.

Housemaster Michaelis clocks your presence as soon as you wanted. He’s stood behind his desk at the moment, presumably because he just bid farewell to the Headmaster.

His grin turns sinister. ‘Close the door behind you, take off your trousers, give me your underwear, and spread your legs in front of me in the desk. It’s time to test your memory.’ Well, he’s not looking to waste time today! Probably just as well; you want to get any punishment he’s planing over and done with.

You get yourself into position without a word, giving the Housemaster your underwear as requested. When you do, he smirks at you. ‘I’m officially confiscating these until further notice. I think it’ll be fun, sending you off to the Headmaster without them. I wonder if he can smell arousal on a woman sat right under his nose…’ you’re about to protest, when he silences you with a look; he doesn’t seem in the mood to even entertain a protest of any kind.

When you’re spread out on his desk, Housemaster Michaelis opens a drawer, and pulls out six carved wooden poles and some kind of gel. The poles look like elongated wooden bullets, right down to the dome shape at the tip. You’re about to ask what they are, when his eyes silence you once more.

Housemaster Michaelis picks up one of the poles, and begins twirling it absentmindedly in his hand. ‘I was planing to save this punishment for later, but the Headmaster’s visit has me rather pent up, and I long to see debauched in some way. 

‘As you can see, I have six of these charming wooden devices in front of me. I designed them myself for this little game. Now, each one represents one part of you that I named last week. I’m going to ask you the names of each part in turn, and should you fail to give me its name, I shall coat it in this special fluid I’ve acquired, and inset it into your virginal opening. Oh, and before you ask, yes. Yes I do intend to leave them in their as I insert the others, so I do hope you were paying attention last week, or you’re going to find yourself struggling.

‘There is one more rule. As you quite obviously already know what an anus is, I’m not going to waste my time asking that. Instead, should you fail to name all five of the other parts of your anatomy, then this sixth one shall be inserted into your anus instead. 

‘Once the test is complete, we’ll evaluate your progress so far, and see if you’re ready to take things further next time. When that’s sorted, I’ll consider removing my toys. Now then, shall we begin?’ You don’t know why he’s asking; you’re pretty sure he’d do it regardless.

Still, you have to say something. ‘Please Sir, I’m so sorry, but I can’t remember any of last week’s lesson. I tried to find a book to help me, but the librarian is worse than useless. I don’t know if I can take all of those poles in me at once. Please have mercy on me.’ It’s seems pointless to ask such a thing; when has he ever shown mercy?

To your surprise, he doesn’t actually seem that angry. ‘I see. Well, since you came clean like a good girl, I’ll forgo the final part of your punishment. However, I know for a fact that you can take anything I dish out. So, I’m still going to put my toys inside of you, and you’re going to thank me for it, aren’t you? Aren’t you? Or do I have to run after the Headmaster?’ Well, at least he’s relented somewhat; you weren’t expecting that.

You shake your head. ‘You don’t have to get him, Sir. I’ll do my best to take your punishment. But, if it gets too much, will you stop?’ The hell he will, you’re just going to have to accept it.

To your surprise, the Housemaster leans in and gives your forehead a quick kiss.

He gently strokes your face as he answers you. ‘If it becomes truly unbearable for you, I shall stop. There’s no point in me causing you mindless pain. However, your body shall soon have to accept something much wider than these toys of mine; the more prepared you are, the less that it shall hurt when I finally stake my claim.’ For a man that could force you into anything for the sake of keeping your secret, your Housemaster truly can be lenient when the mood takes him.

One final smirk is all the warning you get before you feel something hard and cold at your entrance.

You’ve been so busy listening to your Housemaster speak that you neglected to see what the hand not touching you was doing. Evidentially, it was unscrewing the lid from the bottle of fluid, tipping a pole into it, then lining it up with your entrance, planning to penetrate you at a moment’s notice.

That moment is apparently now, as the pole slides into you, meeting very little resistance as it makes itself comfortable inside your body.

You sigh, not expecting your Housemaster to push it in so deeply; you can feel it nudge against something else inside you, presumably another part of your reproductive system.

Housemaster Michaelis confirms this. ‘Ah, I appear to have reached your cervix. The easiest way to describe the cervix is that it’s the gateway between your vagina and your womb. The opening of the cervix is small enough to allow sperm in, and menstrual discharge out. Naturally, it will also widen enough to let a baby pass through, but we needn’t concern ourselves with that. No, all I’m interested in is filling up your vagina. Tell me, how does it feel, having something seated inside of you like this?’ You don’t know. It feels… different. Slightly uncomfortable, certainly, but there’s something else. Pleasure maybe? It could be, but you’re not sure.

You vocalise your observations, and Housemaster Michaelis nods thoughtfully. ‘That sounds about right. It does take women a while to become used to having things in their vaginas. I think another pole may help you get your thoughts in order.’ He selects another of his toys from the pile, and this time you get to watch as he sticks it into the jar and coats it in fluid. You’d initially believed the stuff in the jar was closer to water, but on closer inspection it seems to be more viscous than that.

Before you get the chance to ask what it is, Housemaster Michaelis inserts the second pole, and your walls clench around it, clinging on tightly to both intrusions. This new one seems to be going to be just as deep as it’s twin, and you’re certain the others will be joining them there soon.

As you try to adjust, you hear a silken voice speaking to you. ‘Can you recall the name of the part of you this toy is rubbing against? Think carefully now.’ Shit! What was it again? It wasn’t quite the womb, and they’re in the vagina…

Oh, you’ve got it. You think… ‘The cer-cervix, Sir?’ You answer tentatively.

Your Housemaster smiles at you. ‘Good girl. Such a good girl. Almost makes me feel guilty for sticking wood into you; you deserve something much better. Now, ready for the next?’ You nod, not wanting to disappoint him. Besides, he’s already managed two, which is more than you’d expected to take. This third may well be your limit though; you only hope he was being genuine earlier.

The next pole is prepared in the exact same way, only this time you don’t watch it; you’re worried that doing so will only make you more nervous. Instead, you close your eyes and try to relax, thinking about anything else other than that next pole.

You’re just about to start imagining how Housemaster Michaelis looks totally naked when you’re stretched open ever wider, this next one bordering on being too painful. You almost beg Housemaster Michaelis to stop, before he does so of his own volition. 

You open your eyes, and when you look at your Housemaster, his face is a picture of concern. ‘Is it too much too soon? I know you can take it, but it will hurt for the first few times. Still, I confess I’ll be disappointed if you can’t take three; it’ll mean you need even more training than I’d initially thought.’ You tremble at the thought of more training, a rush of heat traveling down to your groin. The heat seems to bring more lubrication with it though; enough to convince you to try this one more time.

You shake your head vehemently. ‘No, Sir. I can take this third one all the way. I’m not sure if I can do four yet though…’ You’re secretly relieved that you spoke up earlier. If you hadn’t, you’d be looking at five poles in your entrance, and one in your rear. In fact, you may still end up like that; there’s nothing you can do to stop your Housemaster, should he decide to do what he had originally planned anyway.

Your statement isn’t answered verbally; it’s answered by Michaelis pushing the third pole in the rest of the way, giving you no time to think as it joins the others.

A moan leaves your mouth, much to your surprise; such a painful intrusion should have earned a cry of pain. However, you can’t deny just how right it feels, being so filled up. You’re even willing to bet that you could take all five rods if you had to, but you’d rather not; you just know you’re going to be sore later, and having even more things inserted into you won’t help matters.

Thankfully, it seems that your plea wasn’t lost on Michaelis, as he makes no move to grab a forth pole. Instead, he walks around his desk in a circle, his eyes trailing your body. 

When he’s done a full circuit, he grins malevolently. ‘Good girl. You look so… well, words fail me. It’s like my own private work of art. Oh yes, I am going to have so much fun with you next time.

‘Speaking of, you’ll be glad to know there is no homework this week; well, I suppose there is one; no masturbation. I want you ready to explode when you come here next week, though I must insist that you visit me after dinner; I’ll be taking you to my room. Fear not, for I shall make a suitable excuse. You’re a talented pupil, after all; it hardly seems outside the realms of possibility that you’d be willing to help me on a little… extracurricular project. Now then, I think you’ve had enough stretching for now. You’re lucky that seeing you managed to calm my temper; the mood I was in earlier, I would have forced you to take all six toys.’ The thought makes you shudder, as does the fact that all three poles are removed at once, the sudden lack of an intrusion coming as quite a shock.

With nothing now between your legs, you close them, before sitting up and slicing off the the table.

You make your way over to your trousers on shaky legs, almost falling forwards until a pair of arms snake around you.

Housemaster Michaelis’ breath is hot in your ear as he speaks. ‘I fear I’ve neglected both of our needs this time, but not as much as I’ve been neglecting what I’m sure is a magnificent pair of breasts. Fear not, for those hidden globes shall be worshiped by me the next time we meet. I shall endeavour not to be too rough with them; it may make binding hard if over sensitise them. Now, run along to the Headmaster. Oh, and if you find him intimidating, just remember; if the worse should come to pass, you are excellent at fellatio.’ He stabilises your body before letting you go, making sure you don’t collapse.

After taking in a deep breath, you manage to redress, hoping that leaving your underwear with your blackmailer isn’t a horrible idea.

You offer Housemaster Michaelis a smile as you leave his office, one that he actually returns in part; a half smile still counts as a smile.

With your legs still wobbly from your lesson, you make your way to the Headmaster’s office, unsure of what you’ll find when you get there.

**Notes for the Chapter:**

> So, what will the Headmaster have to say? 
> 
> … you’ll have to find out next time ;)
> 
> As always, thank you for reading, and I hope to see you again soon ^.^


	6. Latin Lesson

**Notes for the Chapter:**

> Hey,
> 
> Sorry it’s taken me so long to update. At this point, I’m sure you’re all used to it, but I’m sorry all the same.
> 
> As you may have guessed from the title, this chapter will feature Latin. As someone who pretty much only knows the phrase ‘deus vult’, I had to rely on the internet to help me, so there may be a few mistakes. Also, unlike I have with several fics in the past, I’m not going to add a translation index at the end. I’ve hinted at the translations for all but one line, which you will find out the translation for… eventually ;) do feel free to look it up if you’re curious though; curiosity is never a bad thing.
> 
> I hope you like it ^.^

The walk to the headmaster’s office seems to go on forever. What exactly does he want with you? You wish you’d had the good sense of mind to ask him that a moment ago, but you were so surprised to see him that shock stilled your tongue! Still, it would only have raised suspicion if you had pestered him. Better to feel anxious than to give him a reason to question your validity as a student…

Taking a deep breath (something that seems to be a common occurrence at this point), you do your best to walk to your destination with your head held high. All he knows about you is that you’re a dedicated student, with consistent grades, who isn’t above seeing tuition to better improve yourself. Really, you’re every headmaster’s dream student. In fact, he probably wants to talk to you about your future or something. Maybe he’s heard of a few apprenticeships in London that he thinks you’ll suit? The man is probably trying to do you a favour! You have no reason to believe that he knows your secret. You’re just being paranoid!

Unfortunately, you’re so distracted by your thoughts that you manage to walk straight into the headmaster’s door, your head generating a loud thump on the solid wood. 

As you rub the newly-formed sore patch on your forehead, a voice calls out from the office. ‘Come in if you’re expected. If you’re not, kindly speak to the deputy head instead; I’m in no mood to entertain unexpected guests.’ Well, that’s rather rude. What if a student desperately needs to see him? Then again, the vice head does seem to deal with most things these days…

As you are in fact expected, you enter the office, and take your hand away from the bump on your head. The last thing you want is to draw attention to it, especially given how you injured it; you’d hate to have to confess that your mind was so distant, the physical world seemed to disappear.

The Headmaster is currently day behind his desk, his eyes pouring over pile upon pile of paperwork. When he hears his door open, his eyes flash up, and a slight smile appears on his lips.

He maintains his smile as he speaks. ‘Ah, you remembered to pay me a visit, I see. Please, take a seat. I promise this won’t take long.’ He gestures to a seat across the desk from his own, and you sit as indicated, but not before closing the door behind you; he seems the type of man who would prefer privacy during his meetings.

As soon as you’ve taken your seat, the Headmaster continues talking. ‘So, taking extra Latin lessons from Mr Michaelis, are we? That’s a fantastic attitude, one I wish all of my students had. Would you mind if I tried my hand at testing you? I find that nothing helps one to retain knowledge like repetition!’ Is he for real? This can’t be why he called you here! He didn’t even bloody know that you’d planned to take extra lessons! Unless he decided to invite you on a whim? At this point, you’re not sure you’d put such a thing past him! 

Nevertheless, it’s probably best to comply. After all, if he’s speaking Latin to you, at least he’s not questioning your gender!

You give him a curt nod. ‘Of course, Sir. I would greatly appreciate the practice.’ This is where he used a whole slew of phrases that you’ve never heard before…

The Headmaster looks thoughtful for a few seconds before speaking. ‘Okay, we’ll start off easy. Translate ‘absolutum dominium’ into English for me.’ Wow, he really is starting off easy.

Your mouth forms a confident smile. ‘That means ‘absolute dominion’, Sir. That is to say, complete dominion over something, like you have dominion over this school, and it’s pupils to a certain extent.’ You internally cringe; could you be any more of a sycophant?

Still, the Headmaster seems pleased with your answer. ‘A perfect translation. Let me try something more difficult… mmm… alright, ‘alea iacta est’.’ That one certainly is more difficult, but it’s nothing you can’t handle.

‘It means ‘the die is cast’, Sir. Like the die of fate, I suppose.’ It’s a difficult thing to explain, but he didn’t actually ask for an explanation, just a translation.

A thoughtful hum escapes the Headmaster. ‘So, you’re a believer in fate then? Not one for divinity? You don’t think that maybe there are beings in our world that are more than human?’ That’s an interesting question, one you really don’t know how to answer.

Instead of engaging him in philosophical debate, to take the opportunity to show off. ‘’Haud ignota loquor’, Sir. I’m sorry.’ 

The Headmaster hurts out laughing. ‘My, what a witty pupil I have! I suppose one shouldn’t speak of things that are unknown. Then again, what in this world is truly unknown? After all, ‘acta deos numquam mortalia fallunt’. There is always someone who knows the truth of everything, therefore nothing can be unknown. Wouldn’t you agree, my dear Alumna?’ Your blood runs cold. ‘Alumna’? Female pupil? He knows! Oh God, he knows! How? Did someone tell him? Did he examine your entrance papers and find a discrepancy? All these years of heard work, gone in an instant!

No, no way. This is not how you’re found out. After what you have allowed the Housemaster to do to you for the sake of secrecy, there is no way you’re faltering here!

Feigning confidence, you say the first thing that comes into your head. ‘I fear I must correct your Latin, Sir. You used the incorrect word for pupil. I am an alumnus, not an alumna.’ This is it, the moment of truth. Will he push his point? 

There’s a moment of tense silence, before the Headmaster breaks it. ‘My sincere apologies, dear boy. My Latin must be rustier than I’d thought. Perhaps I should have you tutor me? Would that be a strange suggestion?’ Your heart feels like it’s about to drop out of your ass. You really pulled that off! It was just a common mistake! What a relief!

The smile you give to the Headmaster is sincere. ‘’Homo sum humani a me nihil alienum puto’, Sir, and I think to pursue knowledge is a most human intent.’ You only wish you knew about the Headmaster’s intent. You still don’t know why you were summoned here.

That comment earns you a grin. ‘Indeed, and ‘cogitationis poenam nemo patitur’. Not that I’m suggesting you would punish me for my intent; I am the one with ‘absolutum dominium’, after all. However, I could punish you for attempting to find inappropriate materials in the library last week. Honestly, understand that men have needs as much as anyone, but searching for such illicit material is really not appropriate. The only reason I have yet to do so is because I am a fan of the old adage ‘actus non facit reum nisi mens sit rea’, and I have no idea if your mind is guilty of the lewd thoughts I assume it to be. So tell me, why were you trying to find detailed descriptions of female anatomy?’ Oh. So that’s why you’re here? Well, at least that’s easy to talk your way out of…

Putting on your finest look of contrition, you do your best to fabricate an answer. ‘It was just curiosity, Sir. I mean, all of us here are taught biology, but no one has touched on the anatomy of the living. I’m just curious as to what women look like… down below… so that one day, when I marry, I won’t be surprised by what I see. After all, I’m certain that a woman’s intimate area is far different from my own. That’s the only reason, Sir; I just want to know what to expect.’ That seems a reasonable response, one you’re hoping he’ll believe. It’s not like you can say ‘I’m sorry, it’s just that Housemaster Michaelis wanted me to memorise all the bits of my own genitals. He tried testing me on them, by the way. I couldn’t remember any of them thanks to being denied at the library, and I almost ended up having a pole shoved into my…’

Your train of thought is interrupted by the Headmaster. ‘I see. Well, I can’t say I blame you. There’s not a man around who hasn’t found himself curious as to the workings of the female anatomy. I myself have studied it at length and up close, although you’re not in a position that allows for the practical exploration of another woman’s genitals. Or rather, a woman’s genitals.’ The Headmaster rises from his chair, and heads over to a nearby bookcase. He pulls out a rather dusty-looking book from the shelf, and hands it to you. As you look at the cover, you almost drop it in shock. Is that…?

The Headmaster smirks. ‘I know that ‘The Karma Sutra’ hardly counts as an anatomical text, but if your aim is to understand sexual desire and how best to please your future wife, then this is the book for you. I’ll have to ask that you keep it hidden as best you can, but that book is yours to keep. Consider it my way of passing on knowledge to one of my brightest pupils. I’m sure you’ll find it a most engrossing read.’ Your face starts to burn, a violent blush consuming it entirely before it moves on to cover your neck. You’ve never been more embarrassed in your life! Your headmaster has just handed you a book full of sex! What do you even say to that?!

All you can do is give him a curt nod. ‘Thank you, Sir. This is most kind of you. I shall study the tome as soon as I am able.’ You hope he lets you go now that he has his answer. If this conversation goes any further, you’re going to need a week-long cold shower, and a complete mental wipe.

Unfortunately, the Headmaster isn’t finished just yet. ‘I remember when I was your age. Ah, the things I used to do to myself in my own bedchamber. I used to dream of pretty women in nothing but their smalls, their firm breasts on full display. Oh, how the men of our age have lost appreciation for such things. Most men prefer to take their wives while they are still mostly clothed, still so prude even in private. I just can’t imagine not having a nice pair of breasts to stare at when I make love. So soft, so firm, so enticingly female…’ He places his hands on your shoulders, and your heart begins to speed up. His hands feel unbearably warm, even through your clothes, and his words… you resent not reaching climax at the hands of your Housemaster a moment ago. As it is, your body is so desperately frustrated that you’d give anything to for a little stimulation. Maybe your headmaster would give it to you, if you told him your secret…

No sooner than you think that, the Headmaster takes his hands off of you, before returning to his seat behind the desk. 

He clears his throat. ‘I’m sorry about that. I got carried away. Perhaps I am the one who needs reprimanding after all. It’s just been so long since I felt the soft flesh of a woman beneath me… it drives a man to distraction, you know? Men will do almost anything to bed a woman. They’ll use money, prestige, blackmail… there really is nothing we won’t stoop to. 

‘Anyway, that’s quite enough of that I think. I’m sure you must be eager to return to your studies. You are free to leave.’ You should be relieved, but there’s something in his speech that has you curious.

Making no attempt to move, you decide to ask something. ‘Forgive me, Sir, but I must ask; why do men seek out sex? Surely it can’t be worth sacrificing morality and credibility for?’ That said, you’ve given up your credibility and morality by sleeping with your Housemaster, even if it is an act of circumstantial necessity.

The Headmaster takes a moment to think before answering. ‘It depends. Sometimes the act itself isn’t the real appeal. As pleasurable as it is to sink yourself inside a woman’s gentle heat, few people do it for that feeling alone. Most commonly, it is done when two people are in love, as a way of affirming it. I’m sure I don’t need to explain why that would be pleasurable; it’s human nature to want to be connected so intimately with another. Humans are sociable creatures by nature, and therefore crave making connections with others. To that end, sex is a wonderful thing.

‘For some, sex is only desired for one reason; procreation. In our age, as I’m sure you’re already aware, noblemen desire heirs more than anything else. To produce a son, men will sleep with their woman as often as possible, in the hopes that nature shall grant them what they want. Should they fail, it is not uncommon for them to seek out other potential ‘vessels’ for their young. They will do anything to ensure their bloodline remains.

‘Then you have the other main group, which I’m going to clump into one just to spare you from a lecture. They are the men who use sex for power and control. They have sex not because they want it or because they enjoy it, but because they can. They find themselves a woman that they see as weak, and they force them to have sex just to prove that they are more powerful. They think that shoving themselves into a woman gives them dominion over her, the same way that dogs try to hump the human members of the household. These men have to be the top dog, no matter what. It is best that women avoid such men.

‘I suppose that there are men who just want sex for the feeling, but they’re not hugely common. If only men and women were allowed more carnal freedom. Anyway, I hope that I’ve been of some help. As your headmaster, it does seem rather inappropriate to tell you all this, Alumna. Still, I’ll keep it secret if you will.’ He winks at you, and you begin to grow confused. He almost sounds like your Housemaster does…

You decide to leave quickly, as to avoid revealing something you shouldn’t. You can’t help one finally bit of showing off though…

You stand, clutching the book at your side. Before you leave though, you say one last thing to your headmaster. ‘Vale, Sir.’ You incline your head forward instead of bowing.

The Headmaster does the same, before grinning at you… salaciously? You really can’t tell… 

‘’Sed domi maneas paresque nobis novem continuas fututiones.’’ You stare at him questioningly. ‘You’ll find out what that means soon enough, I promise. See you soon.’ He giggles, and you rush out of the office, your cheeks still warm from your earlier embarrassment.

As you head back to your dorm, you think on the day’s events. Stretched out by your housemaster, embarrassed by the headmaster… and yet, nothing has been gained from either one, other than intense sexual frustration and acute paranoia. That, and you’re banned from touching yourself, despite having the best possible material to pleasure yourself with. Life can be so unfair…

You drop the book off at the dorm before heading off for the coldest shower possible.

**Notes for the Chapter:**

> So, there we go. I hope you all enjoyed it.
> 
> As I said before, no translation index, but Google should be able to answer any questions you may have.
> 
> Thanks for reading, and I hope to see you soon ;)


	7. Personal Visit

**Notes for the Chapter:**

> Hey,
> 
> Sorry it’s been so long! I’ve had a lot on, and for the life of me, I just couldn’t think of any ideas for this chapter. Thankfully, my inner pervert decided to do me a solid, so we now have this! I do hope it’s worth the wait!
> 
> Right then, I hope enjoy ^.^

The evening of your next trip to the Housemaster’s office comes around with alarming swiftness, made worse by his seeming omnipresence the week leading up to said visit.

For an entire week, it seemed as if Housemaster Michaelis was following you, showing up at the most unexpected of times to check up on you (and your fellow students, though you suspect he didn’t pay them half as much mind as he did you). He’d made a habit of pulling you to one side at least three times a day, questioning you on your ‘homework’, and teasing you with all the thing he apparently has planned for tonight.

‘It must be hard, having to abstain from touching yourself.’ He’d said two days ago, his voice dropping with sin. ‘I bet the slightest touch could have you calling out my name. Perhaps I should drag you into the nearest alcove and play with you a while. Doesn’t that sound like fun?’ You’d rejected the offer immediately, knowing it to be a test. 

Instead of being rewarded for your patience, you’d received a few strokes of the cane, the strikes not as intense as before due to your clothing. If only he’d yanked your trousers down beforehand, you could have had some real fun…

Anyway, that was then, and this is now. Right now, you’re outside Housemaster Michaelis’ office door, your fist a second away from making contact with the wood. What does he have in store for you tonight? After last time, you’re inclined to believe that he’s going to deflower you tonight. After all, why else does he want you in his private quarters? It must be a special occasion, and you can’t think of anything more special than having a man take you for the first time…

The door opens before you get the chance to knock, your hand freezing in midair in shock. 

In the door’s place is your Housemaster, his face the very picture of sin. His mouth twists into a licentious smile as his weed roam over your body, clearly assessing you for some reason. ‘Perfect. Exactly on time. Oh, but you do look appetising tonight. My room is this way. If you would follow me…’ he stands aside, gesturing you into the room. Your legs move of their own free will, body already anticipating Housemaster Michaelis’ next move.

His next move turns out to be locking the door, before walking over to a near identical door located the other side of his office. You follow him as instructed, up a flight of stairs and into his private room.

There’s a second door on this floor, one that separates it from the stairs. He locks that one too, ensuring your total privacy for the evening. 

With your privacy sorted, the Housemaster approaches you again, before uttering a single command. 

‘Strip.’ 

It takes a few seconds for his words to register. No one has seen you naked since your nanny bathed you as a child! Yet here you are, being asked to strip by a man who’s blackmailing you into doing so. For the sake of your honour and decency, you should leave this place.

Honour and decency make no move to stop your arms as they begins removing your uniform.

Blackmail or not, there’s something about Housemaster Michaelis that you find utterly hypnotic. Your body doesn’t feel like your own when he’s around; it answers to his commands in a way that it’s never once answered to yours. After all, if it had listened to you, you’d have probably left by now.

You start with your top half, pushing your blazer away without a second thought. Then comes your shirt and tie, once again easily disposed of. The only difficult thing to remove is your binding, something which Housemaster Michaelis is now glaring at.

He shakes his head at you. ‘This in and of itself should be a punishable offence. You dare to hide your breasts from the world? From me? Oh, but I am going to punish for it anyhow. After all, this is my room; I am the one in control. Now, I want these bindings gone by the time I’ve fetched the instrument of my punishment. If they’re not, you’ll earn an additional punishment. Understood?’ You nod furiously, trying to remove them in record time. Knowing your luck, a second punishment will mean orgasm denial, and there’s no way you could cope with that. Housemaster Michaelis has opened a need within you; if he doesn’t fulfil it, you don’t know what you’ll do.

Thankfully, these last few years have made you a master of binding application and removal, meaning that you manage to finish your task first.

When he notices this, the Housemaster pouts. ‘Pity. I was looking forward to caning you again. Never mind…’ he shows you the object he plans to punish you with; they look like thumbscrews with a small chain on the end.

The Housemaster smirks at your evident confusion. ‘They’re for your nipples, in case you were wondering. One on each, to be tightened and loosen as I so will it. I also have a set where the two claps are connected, but these will do for now. Now, if you’d kindly sit on the bed, we can begin.’ That may sound like a request, but you’re certain he means it as a command; fail to do what he says, and he’ll make you do it, then punish you for disobedience. 

Dutifully, you sit on the Housemaster’s bed. The bed itself is a four poster, the wood covered in ornate carving that may be as old as the school itself. You’d love to flop down onto it and sink into the mattress, but you’re certain that would earn you a caning, so you resist the urge. Instead, you’ve sat yourself right on the edge, and put your arms behind your back, puffing your chest out in Housemaster Michaelis’ direction.

The Housemaster smiles. ‘Oh my, but aren’t you being good this evening. I think you’re expecting an extra special reward tonight. Tell me, have you touched yourself at all since our last meeting?’ You shake your head, too excited to form words. You just know you’ll be getting a special treat tonight…

To your shock, the Housemaster frowns at you. ‘Oh dear. You’ve just ruined your streak. You see, when I ask you a question, I expect an answer. Nodding at me like an imbecile is not an answer. I’m now beginning to rethink giving you that reward I thought you wanted so desperately. Such a pity. I was going to have you screaming my name and everything. Perhaps it would be best if you left now.’ What? He’s kicking you out? Just because you didn’t answer his question verbally? What does that mean did your situation? Is he going to tell the Headmaster?!

Terrified he’ll do just that, you decide to plead with him. ‘I’m so sorry, Sir. I should have given you a proper answer. Please don’t kick me out. I’ll make it up to you.’ His eyes gleam menacingly, and you realise you’ve just fallen into a trap…

Keeping his gaze firmly set on you, the Housemaster gives his orders. ‘I have the perfect apology in mind for such an indiscretion as it happens, one I know you’ll be happy to dish out. But first, I think it’s time I showed you how these go on.’ He holds up the clamps in his hand, tangling then in your direction. Anticipation shoots through you; you only hope they aren’t as painful as they sound.

Before you have time to ask that very thing, Housemaster Michaelis launches himself at you, his mouth covering your nipple completely before he starts teasing it with his teeth.

You squirm helplessly on the bed, trying to create friction between your legs. The feeling of have your nipple teased and nipped is foreign yet wonderful, and the lust that flows through is intense. You’re about to consider rubbing your crotch against the Housemaster’s body when he pulls away, once again dangling one of the clams in front of you.

Headmaster Michaelis admires his handiwork before smirking at you. ‘Perfection. I need your nipples hard, or else getting these clams on will be next to impossible. 

‘Now then, I’m going to place the first one on now. I shan’t make it too tight, but should you misbehave, do not think for a moment I won’t tighten it. Understand?’ You should probably give him a verbal answer this time, given how poorly he took your nodding a moment ago…

Your voice doesn’t sound as confident as you’d like it to when you answer. ‘I understand, Sir. I promise I’ll be good now. I’m still hoping I can earn a reward, after all.’ You’re about to flutter your eyelashes, but you think better of it, knowing that such a thing would probably irritate the Housemaster.

Your response earns you a smirk. ‘We shall see. Now then, this may pinch a bit. Feel free to tell me if it hurts; I shan’t stop, but I am curious as to how well you can take certain things.’ With that, he brings one of the clamps to your nipple, places the sensitive flesh between the two clamp heads, and begins to trap your nipple inside.

It pinches, that much become obvious immediately. You’re half concerned it’ll cut off the circulation, but you trust that your Housemaster will be watching for signs of such a thing. 

Trust? More like hope…

As you get used to the foreign object around your nipple, your Housemaster assaults its twin, though this time he decides to slip a hand between your legs, teasing you through the fabric of your trousers. This man will surely be the death of you tonight…

When your other nipple is ready, Housemaster Michaelis clamps it too, just as firmly as he did the first. It feels just as unusual too; these are not something you could ever see yourself fully comfortable wearing.

With both clamps in place, Housemaster Michaelis stands before you, his eyes hungrily devouring your body. ‘Delicious. I could stare at you all day. If the other males in this school got so much as a glimpse of you now, you’d spend the rest of your academic life in the centre of a never-ending orgy. Oh, but I suppose you don’t know what that is, do you? Perhaps I’ll explain later.’ Given the context, you’re willing to bet it involves halving people look at you while they pleasure themselves or something. Unless it’s more involved…

No, it couldn’t be! How are you supposed to have sex with more than one person at a time? It just doesn’t make sense.

Apparently tired of merely looking, Housemaster Michaelis places a hand under your chin, and uses it to make sure you maintain eye contact as he speaks. ‘Now that you’re new toys are in place, you can finish undressing. Then, I want you on your hands and knees, legs parted enough to show me your vaginal opening. I plan to reunite you with some friends of yours tonight; they’ve missed you.’ Friends? What friends? You have no friends, not that he could have with him right now! 

That’s not what concerns you right now though; you’re more concerned about what Housemaster Michaelis didn’t say.

As you stand and remove the remainder of your clothing (nipples aching every time you bend over), you ask a question. ‘Am I to get down on all fours on the floor or on the bed, Sir?’ You’re aware he’s yet to punish your for your lack of words; perhaps having you on all fours on the floor is that punishment.

Your concerned your question will earn you a slap or something; all it earns is a slight smile and an answer. ‘As much as I’d love to see you crawling on the ground like a common whore, I fear it would be detrimental to my plans. You are therefore permitted to return to the bed. Oh, and make sure that you are facing me, rather than the headboard.’ He doesn’t ask for confirmation that you understand him, which is a relief; you’re not sure if your voice even works after that he just said. Is it wrong that hearing such words from your Housemaster’s mouth is a tremendous turn on?

When you’re finally naked, you get into position, watching your Housemaster as he retrieves something from across the room. Your heart stops as you realise what he meant by ‘friends of yours’…

… it’s the wooden poles from your last visit. 

You count them quickly; it looks like he still has all five. Does that means he’s going to see how many you can fit? Or will he pushing you by putting them all inside? You’re beginning to panic now…

Said panic must be evident, as your Housemaster immediately reassures you. ‘Recognise these, I see. Well, fear not. You’ve already proven yourself capable of three, so tonight, I intend to stick four things inside you. If you can take that, I’ll give you that reward you’re so desperate for. If not, then prepare to be disappointed.’ This isn’t fair! You had trouble doing three not so long ago, now you have to take four?! This punishment isn’t fair! Then again, neither is blackmailing someone, but that didn’t stop him from doing just that the moment you were formally introduced. You’re going to be so sore in the morning…

Without another word, your Housemaster walks behind you, and runs a finger over you opening. ‘You’re not nearly as wet as I’d though you’d be. Are you truly that nervous? Or have I yet to do anything to excite you sufficiently?’ You can’t see his face, but you can picture the pout he’s almost certainly doing. You could destroy his ego right now, if you had a mind to.

Regrettably, you lack your Housemaster’s sadistic streak, so you answer truthfully. ‘It’s nerves, Sir. I’m still so new to all of this.’ You’re mostly just relieved that nobody else knows about these ‘meetings’. If your father knew what you’d been up to, he’d disown you, family business be damned!

The room is filled with silence for a moment. Then, without warning, Housemaster Michaelis begins teasing your opening with his fingers, before leaning his head in closer to yours.

His voice resonates with sin. ‘You’d do well not to remind me of your inexperience. Oh, but how I crave taking it from you. My mind is constantly consumed by thoughts of you, and how I’m going to ruin you completely. I’ve considered deflowering you on my desk, in the library, in my bed… I’ve even considered sneaking into the Headmaster’s office with you, just to add danger to the situation. There is one thought that I enjoy the most though. Shall I tell you what that is?’ It takes everything you have to choke out the word ‘please’, which is mercifully enough to keep the Housemaster talking. ‘Alright then. The fantasy that consumes me the most is one in which I sneak into your dorm at night, crawl into your bed, wake you with a few harsh nips to your neck, and steal your innocence like a thief in the night, right underneath the noses of everyone in your dorm. It would surely make for delightful viewing, watching you stifle your moans for fear of waking them. I’d still try to tease them from you, but you wouldn’t give in, would you? You’d keep your pretty little mouth closed, for fear of everyone finding out the truth. That is your greatest weakness, after all. Well, that and some basic stimulation, it would seem; you’re positively dripping now.’ He slips a finger inside to illustrate his point, and your whole face reddens at the obscene noise that follows.

Housemaster Michaelis removes his finger just as quickly as it put it in, before placing the digit in front of your face. ‘Suck.’ You can’t do it. He can’t honestly expect you to taste yourself, can he? That’s obscene!

When you make no move to obey, Housemaster Michaelis moves his hands down to your breasts, tightening both clamps. You wince, unprepared for such a sensation. As sore as it’s made your nipples, you can’t deny that the sensation is fast becoming quite enjoyable…

Unable to contain yourself, you let out a moan, something which seems to anger your Housemaster. ‘The point of a punishment is that you’re supposed to hate it. I fear I’ve underestimated just how much of a whore you are. Now, you can either taste yourself, or I can tighten those clamps until it’s cuts off your circulation. I doubt you’ll be moaning when you have to see the nurse tomorrow, now will you? So, I’ll tell you one more time; suck.’ He places his finger barely an inch from your lips, and this time you comply, closing your eyes in embarrassment.

To your great surprise, it’s not as unbearable as you’d thought. It’s not the most pleasant taste, but it’s tolerable. If you had to do it again, you would.

Satisfied, Housemaster Michaelis withdraws his finger, wiping it off on your bottom lip. He doesn’t say another word, but you can hear the sound of wood hitting wood behind you; he must be preparing those ‘toys’ of his.

Sure enough, within seconds he has one of them buried within you, it’s tip nudging the entrance to your womb again. 

It feels much the same as it did last time, a great surprise given the lack of external lubrication; you really must be ‘dripping’, in that case.

Apparently feeling sadistic tonight, Housemaster Michaelis twists the object inside you, a low chuckle escaping his throat as you cry out at the sensation. You can’t decide if it feels right or wrong, but one thing is certain; it feels so good.

Satisfied that you’re handling it well, Housemaster Michaelis inserts another one, once again pushing it fully inside. The stretch aches a little this time, but it’s not quite as hideous as it was last time. Maybe you’ll be able to take three, after all…

As soon as the third one slips inside, you know such an assumption was a mistake.

It still aches just as much as it did the other day. The stretch is too much. How are you supposed to take four of them? It’s still too much too quick. You just can’t do it!

To your great relief, Housemaster Michaelis stands, leaving the two spare poles on the bed. He stalks around the bed slowly, taking in your current state. You can see a bulge forming at the front of his trousers, a clear sign that he very much likes what he sees.

When his viewing is complete, Housemaster Michaelis stands before you, his trademark smirk in place on his lips. ‘Days like this, I really wish I had one of those newfangled camera machines. Oh, but how I’d love to commemorate this occasion with a photograph. It’s just as well I have a perfect memory, really. 

‘Well, now that I have you ready, I think it’s time I gave you that punishment.’ His unzips his trousers and pulls his underwear down enough to reveal his erection, the very tip of it leaking in anticipation. ‘I believe I told you I’d be placing four things inside you. In case your current state has destroyed any cognitive functionality, this is number four. I think this is a fitting punishment for you; you refused to use your mouth to answer me, so now, I’m going to use your mouth. So, be a good girl, and open wide. Oh, and I still expect you to swallow down every last drop of my release. As much as I’d love to see you covered in my release, that’s a sight for another day.’ He walks closer to you, and you open your mouth as requested. You wonder if it’ll be the same as it was last time. Does he expect you to tease him with your tongue? Should you position it as such? Maybe you should as-

Before you get the chance to even consider asking, Housemaster Michaelis unceremoniously shoves himself inside your open mouth, causing you to gag. He gives you a few seconds to get over it before slipping out and ramming himself back in, his hand grabbing a handful of your hair to keep your head in position.

From there on out, his pace is brutal, Housemaster Michaelis forgoing you comfort in favour of pleasuring himself with your mouth. The force of his movement makes your whole body shake, bringing your attention to your nipples; they feel amazing. It’s like someone is underneath your body, teasing and tugging them constantly. It’s sending a mass of heat straight to your groin, something that’s somehow made even better by the wooden things inside you. If this is what sex feels like, you’re tired of being a virgin. You crave having Housemaster Michaelis inside of you, any aching or pain be damned. If only you had something stimulating that little bundle of nerves above your opening. Just a few brushes of something against that, and you’d fall apart in seconds.

Housemaster Michaelis seems to realise this, as his voice sounds out above you, his tone remarkably calm and collected given where his erection is. ‘I imagine you’re desperate for release right now, aren’t you? I bet you’d do anything I wanted in exchange for something to rub your clitoris against. Well, as your behaviour has been… acceptable, I think you’ve earned a reward. However, I’m not going to give it to you. You have until I fill your mouth with my essence to push yourself over the edge. Fail to do so, and I’ll spend the rest of the night denying you release until you beg for me to fill you up properly. Your time starts now. Best of luck.’ Bastard! That’s a cruel task, evil almost. What if the pressure is too much? What if you can’t finish? You’re going to have to think fast…

Oh. Your hand! If you’re careful, you can balance yourself on one hand, while pleasuring yourself with the other! It’s going to be a challenge, but you have to try, before your Housemaster drives you insane with his torturous plan.

Cautiously, you place your weight on one hand before taking the other away, directing it at your clitoris. Your body sways around worryingly, and for a moment you’re convinced you’re going to collapse. That is, until Housemaster Michaelis intervenes, using the hand not already threaded in your hair to keep you upright. 

His small act of mercy ends up being your saving grace; no longer concerned about falling over, you begin pleasuring yourself in earnest.

It takes less than a minute for you to fall apart.

It’s just as well you were so swift; your Housemaster finishes seconds after, filling your mouth with his release.

Satisfied and exhausted, it takes all of your strength to stop yourself collapsing into a heap on the bed. The same can’t be said of Housemaster Michaelis, who tucks himself back in without so much as a tired sigh, before walking down your body to remove the objects still nestled inside you.

When they’re all removed, he helps you to lie on your back, getting you comfortable before removing the clamps. They tingle like mad as the blood starts rushing back into them properly, something that seems to spike your arousal again. Not that you intend to act on it; right now, you’re struggling to do anything more taxing than lying down.

With everything removed, Housemaster Michaelis manages to get you under the covers, a fond smile on his face. His voice seems softer now; whether it actually is, or if it’s just that your body is so tired you can’t ear properly, you can’t say.

You definitely hear his word though. ‘Rest now. You were extraordinary tonight. I have a few papers to review, so I’ll be sitting just over there.’ He gestured to a desk you hadn’t noticed before. Why does he have a desk in here if his office is literally a small flight of stairs away? ‘Should you wake to find yourself in need of a glass of water or the like, you have but to ask. You indulged me wonderfully tonight; if I can indulge you at all, just say the word.’ Is that so? Normally, you’d be too afraid to ask for anything. However, given that your mind isn’t all there still, you decide to push your luck.

You give your Housemaster a sleepy smile. ‘Does that mean you’ll wake me with a cup of tea?’ You doubt it. He’s just using you, after all; if he really cared, he wouldn’t be blackmailing you.

Still, your request earns you a smile. ‘A cup of tea for the lady it is. In fact, as you’ve been so good to me, I may even bring you breakfast in bed. However, that is tomorrow, and this is now. Right now, the only thing you should concern yourself with is sleep. I hope you find my bed to your liking. If not, then that’s unfortunate, as you’ll be seeing rather a lot of it in the coming months.’ He leans down, and does something you’d never expected; he kisses you once on the lips. It lasts for barely a moment, but you can feel your lips tingling long after the fact. Is this becoming more than blackmail?

You have no time to think on it further, as you soon find yourself drifting off into a deep sleep.

**Notes for the Chapter:**

> Again, sorry for the delay, and I hope it was worth waiting for. 
> 
> Until next time, thank you for reading, and I hope to see you again soon ^.^


	8. Secret Meeting

**Notes for the Chapter:**

> Hey,
> 
> Sorry to keep you all waiting so long! I only hope that it’s worth it…
> 
> Here you go!

It’s unbelievably hard leaving Housemaster Michaelis’ bed.

You feel like someone’s turned your legs to jelly. What did that man do to you last night? Well, other than the whole ‘clamps-on-your-nipples-and-rods-in-your-nethers’ thing… you still can’t believe he did such a thing! Sure, you weren’t certain of his precise intentions, but that was the furthest thing from your mind; you’d half-expected him to take your virginity last night. 

He may as well have done such a thing. Surely it’s not going to be much more strenuous than that was?! The man is a demon in the bedroom, especially when it comes to bringing your body to its limit before going just that little bit further…

As you sit up in bed, your whole body screams out in protest, not least you’re stomach, which seems to be trying to eat itself right now. With all the energy you used last night, that’s hardly a surprise. You’ll have to get dressed and head for breakfast as soon as you can.

Just as you’re about to leave bed, something occurs to you; where is Housemaster Michaelis? He said last night he’d be at his desk, but a quick glance over in that directions shows it to be quite empty. Has he left you already? Did he have somewhere to be? What time is it anyway? Have you slept in?! Oh shit, now you’ve really got to get out of here!

As you tumble out of bed (in a painfully literal sense), the door to the room opens, and you try to cover yourself with the bed sheets in a blind panic, terrified the intruder will discover your secret. Then again, they’d already discover that you’d slept naked in a teacher’s bed; at that point, is gender actually an issue?

To your relief, you recognise the voice of your visitor long before his appearance registers with your hazy mind. ‘Going somewhere, are we? Silly girl, I do believe I mentioned breakfast in bed. Now sit up in bed like a good girl; while I may be training you rut like an animal with me, I don’t except you to eat like one.’ He’s returned! Housemaster Michaelis is back, and he’s got food!

You clamber back into bed with urgency, not wanting to disobey him while he’s in a good mood. You’re still throughly confused though; why treat you like this when he’s got you over a barrel? He could be nothing but cruel if he desired. Why take the time to be kind and respectful when you’ve so little choice in all of this?

Your thoughts must show on your face, because Michaelis frowns as he hands you the tray. ‘Am I sensing suspicion? Do you think this a trick of some kind? I assure you, this is no ruse. It’s all quite simple, really. You have, for the most part, been wonderfully obedient, and more than willing to submit to my every whim. As such, I think it’s only fair that I treat you properly. Consider it a reward for good behaviour. Continue to act as such, and there will be many more rewards to come in the future. This arrangement of ours is very much one of take and receive; I take what I want, and you’ll receive what I believe you’re owed in response. These little treats don’t affect my vow of silence either; if your legs remain open, my mouth remains closed.’ At least you know where you stand with him now. It’s good to know he’ll actually make an effort to be nicer to you after he’s taken what he wants. Though at this point, it’s fast becoming something you want as well…

With no reason to be suspicious now, you begin to tuck into the food Michaelis had given you, marvelling at its taste. Seriously, it’s far above the usual slop that they serve here; this is beyond merely ‘edible’.

The approval must show, because your Housemaster chuckles. ‘It’s good to know you’re one to notice fine food when you receive it; I made this for you myself from scratch. Only the best for my most special pet. So perfectly mine…’ his crimson eyes burn with intensity for a moment, before tailing off into a smoulder. ‘When you’re finished, leave the tray and the dishes here. You’re then to dress, and return to school as usual. If anyone questions your absence last night, you are to tell them that, as punishment for the incident that happened between us on my first day, you were helping me arrange my files, and eventually fell asleep at my desk. If they notice that you’re sore at all, it’s because of the awkward angle you slept at. Repeat it back to me.’ He’s really thought all of this through, hasn’t he? 

Swallowing your mouthful, you exhale, putting on your best ‘this sucks’ voice. ‘Housemaster Michaelis forced me to help him with some paperwork just because I walked into him on his first day. I stayed up so late I fell unconscious at his desk, and he didn’t move me all night, the git! Now I’m all sore. It’s going to take so many baths to get my muscles back to normal…’ you rub your neck for good measure, to try and add extra emphasis. 

Housemaster Michaelis chuckles darkly. ‘My my, but it seems that I have an actress on my hands here. Be careful though; if I know you’re a good liar, I might not trust you.’ As if he’ll ever trust you anyhow…

You play his comment off as nothing, trying a dark smile of your own. ‘Keep making me food like this, and I’ll never lie to you.’ You take a sip of tea, trying to keep your focus as his eyes grow intense again.

The Housemaster smirks. ‘Anything for my little pet.’

-/-/-/-/-/-/-/-/-/-/-/-/-/-/-/-/-/-/-/-/-/-/-/-/-

After leaving Housemaster Michaelis’ office, you begin your day as planned. As you have some free time first thing, your first move is to head to the showers, which are mercifully as vacant as they always at at this time (the other members of your dorm preferring to shower either before breakfast or after dinner). When you’re all dried off, you decide to spend some time in the library, despite its close proximity to a certain someone’s office. After all, if you deliberately avoid him, people are bound to grow suspicious…

Before you can get to the library, a familiar face comes rushing towards you; it’s the younger boy that told you to meet your new Housemaster a while back! Is he running more errands or something?

If he is carrying news, it must be grave; the poor boy is as white as a sheet!

As he stops in front of you, you realise that the news he has is for you.

He’s panting, but soon regains his breath, an expression of concern you hadn’t seen before on his face. ‘There you are! The headmaster has requested that you head to his office immediately! He says it’s urgent. He thinks someone has entered the school under false pretences, and it looks like you’re a suspect!’ Now it’s your turn to turn white. He thinks… oh shit. He knows. He knows, he knows, he knows! You thought you’d gotten away with it last week when you’d visited him, but you hadn’t! He knows you’re female, and that’s it. He’s going to kick you out for sure!

You nod sheepishly. ‘I’ll go and see him now then. Thank you for the message.’ You walk off immediately, wanting to get this over with. To think that everything you’ve worked so hard for is going to be thrown away in a single moment…

No way. You’re not letting this be the end. You’ve worked too hard, learned too much. Add to that your ‘private lessons’ with your Housemaster, and you’re just not ready to leave yet. After all, so far it’s only speculation. Until the Headmaster demands that you strip naked in front of him, he can’t know you’re a woman. Besides, all that boy said was that someone was here under false pretences. That could mean almost anything! There could be an exam cheat or something. You won’t know for sure until you’ve spoken with the man…

… something you’ll be doing right now; you’ve arrived at his office.

You make to knock, but a voice stops you. ‘I’ve been expecting you, alumna. Come in, and lock the door behind you; I have some delicate questions I need to ask you.’ Shit. He knows. He knows for sure. Should you just walk away now or…?

No, you’ll go through with this. It could still be about anything. Anything at all. You can still get out of this!

It’s just concerning he’s still calling you ‘alumna’.

You do as the Headmaster instructed, slipping into the room quietly before closing the door with a dull ‘thud’. A quick twist of the key, and you’re officially locked in with the Headmaster.

Now there’s nowhere left to run.

As you make your way over to the Headmaster’s desk, you almost freeze in shock; is the man in front of you truly the Headmaster?

The few times you’ve seen the man in the past, he’s always worn a large top hat, and a small amount of hair covering his eyes. This man however…

A mass of silver hair cascades all around him, so much so that it covers parts of his arms. The hair that would fall over his face has been swept back over his forehead, revealing what must surely be the face of an angel or something. While there is a slight scar that travels from his the jaw on his right side to the eye on his left, there is no denying that this man is beautiful, and the moment you look into his unusual yellow and green eyes, it feels as if you’ve been hypnotised by your own want.

At your reaction, the man before you smiles, lazily twisting a few strands of his hair through his slender fingers. ‘You came faster than I was expecting, my sweet. I would normally tell you to take a seat, but I’m afraid there is a grave matter we must discus, one that may well require immediate action.’ That voice; it IS the Headmaster! Oh dear. Why is he suddenly so attractive? He’s on-parr with Housemaster Michaelis at the very least, maybe even a little more so. Why is your life now filled with such attractive men? It’s such a distraction…

Still trying to collect your thoughts in the wake of this development, you take a breath, and do your best to answer calmly. ‘A grave matter, sir? What is it? I’ll help in whatever way I can.’ Hopefully offering to comply will help remove any possible guilt you might have projected lately…

The Headmaster’s expression grows grim. ‘It’s quite serious, I’m afraid. I fear that our latest member of staff, Housemaster Michaelis, may have an ulterior motive for coming here this year. I suspect that he is here on external business, and has a student assisting him. Normally I would shudder at the thought of implicating one of my finest students in all of this, but I can’t help but notice you’ve been spending a lot of time with him, alumna. Therefore, it is with regret that I must ask you to submit to a quick search. I won’t be too intrusive, and you can refuse of course, but doing so will only give me more reason to suspect you. It is entirely your choice.’ A search?! What kind… this can’t be good. Does he just want you to turn out your pockets, or is there more to it than that?! Maybe you should just refuse, and let Housemaster Michaelis cover you…

No, you’ve got this. He said a quick search, after all. He won’t be too intrusive. The worst you’ll have to face is a pat down, and it’s not like he’ll deliberately pat your crotch. If he notices that your chest is a little smooshy, you’ll just have to say that you’ve put on weight recently, and have therefore been trying to hide your flabby chest. That even explains the bindings! It’s genius!

Therefore, you nod. ‘If such a thing would help, I’d gladly allow you to search me, sir. What would you have me do?’ As long as it doesn’t involve taking all of your clothes off…

The Headmaster grins, and you feel a jolt in your stomach. Nerves maybe? Or something more… ‘I appreciate your cooperation. I’m sure we can have this matter sorted in no time. Now, if you’d kindly hand me your blazer, I need you to put your hands on the wall over there. Then I’d like you to bend over slightly, and spread your legs apart enough so that I can pat them down. I doubt that Housemaster Michaelis would give his accomplice a weapon, but as this is a school, I don’t want to take any chances.’ So, it will be a physical search, after all. At least you have your strategy now…

Without hesitation, you hand over your blazer. ‘Here you are, Sir. I can promise you now that I’m not carrying any weapons, but if searching will exonerate me, then I still consent to being searched.’ You walk over to the wall, positioning yourself as instructed.

The Headmaster searches your blazer, making sure to check all of the pockets. When he’s done, he walks over to you, positioning himself only an inch or so away. ‘Nothing suspicious in your pockets. Not much of anything, in fact. It’s a shame. I was half expecting to find explicit material in them after our last conversation. Perhaps I misjudged you. Maybe you’re not that into women, after all…’ What does that mean?! Is he… disappointed? Did he think you some kind of sexual deviant? Maybe that’s why he’s suspicious of you; if you’re deviant in one sense, why not more?

You’re about to say something, but you immediately forget what it was; the Headmaster untucks your shirt from your trousers, and pushes your shirt up a little. 

His hands caress your sides, stroking your gently from your hips to the bottom of your ribs, and right back down. ‘Such wonderful curves, alumna. So soft. So shapely. So feminine…’ Your heart drops; he’s known all along, hadn’t he? He’s just doing this to make an example of you, to toy with you before he kicks you out. It’s all been for nothing, all these years for nothing…

You take your hands off of the wall, and you’re about to turn around and face him when he grabs your hands and puts them right back where they were. 

The Headmaster leans in, his voice caressing your ear. ‘Ah, ah, ah. Stay still. I’m not finished yet. I still have to search you for weapons, remember? Unless you’d like to tell me something… something I don’t already know, of course.’ What can you possibly tell him that he doesn’t already know? Right now, the best thing to do is remain silent, and pray that he doesn’t humiliate you…

When his question receives no answer, the Headmaster slides his hands down your arms to your hips, then around to your front. He begins to slowly unbutton your shirt, and his teeth begin nibbling at your ear. He moves forward until his crotch is flush against your ass; he feels fully erect, and you begin to wonder if he’s planning to do what Housemaster Michaelis has yet to do…

You wonder if he’s the man you’re going to lose your innocence to. 

The Headmaster has to pull your tie loose so he can access the final buttons, and once he has, he begins to work on your bindings, words now forming between nibbles. ‘I know… you’ve got… weapons… on you…’ he temporarily abandons trying to free your breasts to cup when they’re hiding, his crotch bumping against you forcefully. ‘I’m going to… see if they… work properly…’ he moves back to the bindings, and you can already feel that you’ve ruined your underwear. Despite the situation, and despite already being involved with one teacher… the Headmaster is driving you wild, and he’s barely done anything!

When the bindings are gone, the Headmaster uses them to bind something else; your arms. He grabs your hands and brings them both behind your back, before tying them as firmly as he can without cutting off blood flow. When they’re immobilised, he pulls you flush against him, his hands on your bare waist and his mouth at your ear once again. 

His voice is husky enough that he almost sounds like a different person, and there’s a hint of something almost primal in his tone. ‘I know you’ve been fucking Michaelis, alumna, and I must say I’m disappointed. A woman like you could do so much better than a beast like him, but I suppose I’m not one to talk. Still, it does put you in a most interesting position. I have an important job for you.’ Why do you get the feeling that’s an innuendo of some kind? 

Still, you’re in no position to at least not hear him out. ‘I’ve not… we’ve not going that far yet, but yeah, we’ve been… what’s the job, sir?’ It’s going to involve sex, of that much you’re completely certain…

The Headmaster hums. ‘You haven’t? Interesting… Well, the job is quite simple really. I wasn’t lying to you earlier; Housemaster Michaelis is up to something, and I’d like to know what. As you’re close to him, I thought I’d ask you to keep an eye on him for me. Report back any suspicious activity.’ That’s all he wants? Information? If that’s the case, then…

You nod, but your brow furrows in confusion. ‘I can do that, sir, but I have a question; if all you want is information, why am I half naked and bound?’ Is this a contingency plan? If you’d refused him, would he have kicked you out? 

The Headmaster chuckles darkly, and the sound is the last straw; your underwear is now unsalvageable. ‘I already told you, I need to see if your weapons work. I’ve already made my opinion on breasts clear, and yours… they are quite magnificent, my dear alumna. 

‘So, this is what we’re going to do. As I think it would be unfair to deflower a maiden on my desk, I just want you to rub your bare sex against my erection. Meanwhile, I am going to suck on these perky little tits of yours until I’ve had my fill. When I’m satisfied, you can go in your merry way, straight back to your Housemaster. I expect you back here this time next week for a full report on everything that you learn, and that transpires between the two of you. 

‘Of course, it goes without saying that while you’re helping me with this, your position in this school is quite safe. I’ll also warn you that if Housemaster Michaelis discovers your mission, there will be… consequences. Expulsion, for instance.’ Well… shit. You’re just glad he’s not planning to shove anything anywhere, but still, this is quite the turn of events!

There’s one more thing you need to know, but it might have to wait; the Headmaster has already forced your trousers and underwear down your legs, and is removing his own; your eyes grow wide as his impressive erection springs forth.

His grin is so wide you’re scared his face is going to spilt in half. ‘Bigger than what you’re used to?’ Not by much, but he’s certainly not lacking!

As the Headmaster sits back on his chair, you approach nervously, deciding that now is the time to ask your question. ‘Will I… will I be getting used to it, Sir?’ That was probably an awkward way of phrasing it; does he understand?

The Headmaster grabs your hips, preparing to lift you onto his lap. ‘Put it this way; while I won’t take your virginity on my desk, the moment that is no longer an issue… but for now, things like this,’ he pulls you onto his lap, and begins rubbing your soaked flesh against his erection. ‘Are things you should start getting used to. Also, don’t call me ‘Sir’ when we’re doing this; I’m not your teacher right now.’ He illustrates his point by going straight for your nipple, his mouth latching on firmly before he starts sucking at it with wild abandon.

While he’s preoccupied with your breast, you try to move your hips, trying to rub yourself against him; he never said that you couldn’t enjoy this too. In fact, he seems to be actively encouraging it, his hands on your hips helping you to keep your balance as you try to build up a rhythm.

The Headmaster moves to switch nipples, muttering as he does. ‘So wet… would it be greedy of me to ask you here twice a week?’ Does he expect an answer? You’re a little too far gone for that now, given how close you’re getting to climax. You’re honestly surprised at how wrecked you are, but then again, last night was your first climax in a week; you’re either still feeling sensitive, or the Headmaster is just that good.

As the Headmaster moves his hand behind and underneath you so that he can stick two fingers into you the moment he latches onto the other nipple, you’re pretty sure it’s the latter.

A few clever thrusts and nibbles later and you’re done for, trying not to scream as your eyes slam shut and you tighten around his fingers. 

It takes a while to come down from your high, as the headmaster seems to be drawing it out, his movements still deliberate and earth-shattering. He’s still hard against you, and you begin to wonder if he’s doing this to give himself more time to finish.

Then, out of nowhere, it all stops.

The fingers inside of you withdraw, and his mouth detaches itself with a sinfully wet pop, a small trail of saliva following it. 

In an instant, you’re lifted up, and put down carefully on trembling legs, the Headmaster’s hands keeping you steady as he stands too.

When he’s certain you won’t collapse, he removes his hands, and undoes the bindings on your arms before rubbing them down, trying to make sure your circulation wasn’t cut off.

As he bends down to pull your trousers up, you regain your composure enough to ask an obviously question. ‘What about you? I thought you didn’t want to stop until you were satisfied?’ Did something happen? Why did he stop?

The Headmaster turns you around, picks up the bindings, and coaxes you to lift up your arms so he can cover your breasts himself.

He smiles softly as he answers. ‘I’m plenty satisfied. Watching a beautiful woman fall apart on my lap was spectacular. I will admit that I won’t always let you off so easily, but for today, we’re done here. I’d suggest showering before visiting Michaelis; the man has an inhuman nose on him, and we can’t let him figure us out on day one, can we, alumna?’ If he’s calling you that, it’s looks like you’re back to being his student…

When the bindings are done, you take over, buttoning yourself up. It occurs to you that the Headmaster didn’t actually remove much of his own clothing just now; perhaps the real reason he cut things short was to avoid questionable stains? Either way, if he’s sure that its enough, you won’t push him; you’re certain he’ll have you making up for it in time.

When you look presentable again, you make to leave, only for the Headmaster to grab your wrist before you get too far.

You’re about to ask him if he’s changed his mind, when he gives you something; your blazer.

As you shrug it on, the Headmaster kisses your cheek, making you blush. 

The blush deepens when he whispers ‘should you find that you do wish to visit me outside of office hours, my private quarters shall always be open to you, should you wish for a more comfortable setting for our little rendezvous. Bye for now, my sweet alumna.’ You rush for his office, your face so hot you feel like it’s going to explode! That certainly was an interesting meeting with the Headmaster.

You just have to make sure your Housemaster doesn’t find out.

**Notes for the Chapter:**

> … so, I decided to involve the Headmaster, after all. Thoughts?
> 
> Again, sorry to keep you guys waiting. Your patience has been amazing, and I hope I won’t be quite so long next time.
> 
> Thank you for reading ^.^

**Author's Note:**

> So, did y'all like it? Worth continuing? I do hope so, as I have a few plans for this story in mind already.
> 
> Reviews and kudos are, as always, more than welcome, though I do ask that any criticisms be kept constructive (I'd like to know if I need to improve myself, but I'm a sensitive soul).
> 
> Hope to see you all again in the next chapter :D


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